Alkynes as Synthetic Equivalents of Ketones and Aldehydes: A Hidden Entry into Carbonyl Chemistry
The high energy packed in alkyne functional group makes alkyne reactions highly thermodynamically favorable and generally irreversible. Furthermore, the presence of two orthogonal π-bonds that can be manipulated separately enables flexible synthetic cascades stemming from alkynes. Behind these “obvi...
Saved in:
| Published in | Molecules (Basel, Switzerland) Vol. 24; no. 6; p. 1036 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Switzerland
MDPI AG
15.03.2019
MDPI |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | The high energy packed in alkyne functional group makes alkyne reactions highly thermodynamically favorable and generally irreversible. Furthermore, the presence of two orthogonal π-bonds that can be manipulated separately enables flexible synthetic cascades stemming from alkynes. Behind these “obvious” traits, there are other more subtle, often concealed aspects of this functional group’s appeal. This review is focused on yet another interesting but underappreciated alkyne feature: the fact that the CC alkyne unit has the same oxidation state as the -CH2C(O)- unit of a typical carbonyl compound. Thus, “classic carbonyl chemistry” can be accessed through alkynes, and new transformations can be engineered by unmasking the hidden carbonyl nature of alkynes. The goal of this review is to illustrate the advantages of using alkynes as an entry point to carbonyl reactions while highlighting reports from the literature where, sometimes without full appreciation, the concept of using alkynes as a hidden entry into carbonyl chemistry has been applied. |
|---|---|
| AbstractList | The high energy packed in alkyne functional group makes alkyne reactions highly thermodynamically favorable and generally irreversible. Furthermore, the presence of two orthogonal π-bonds that can be manipulated separately enables flexible synthetic cascades stemming from alkynes. Behind these "obvious" traits, there are other more subtle, often concealed aspects of this functional group's appeal. This review is focused on yet another interesting but underappreciated alkyne feature: the fact that the CC alkyne unit has the same oxidation state as the -CH2C(O)- unit of a typical carbonyl compound. Thus, "classic carbonyl chemistry" can be accessed through alkynes, and new transformations can be engineered by unmasking the hidden carbonyl nature of alkynes. The goal of this review is to illustrate the advantages of using alkynes as an entry point to carbonyl reactions while highlighting reports from the literature where, sometimes without full appreciation, the concept of using alkynes as a hidden entry into carbonyl chemistry has been applied. The high energy packed in alkyne functional group makes alkyne reactions highly thermodynamically favorable and generally irreversible. Furthermore, the presence of two orthogonal π-bonds that can be manipulated separately enables flexible synthetic cascades stemming from alkynes. Behind these "obvious" traits, there are other more subtle, often concealed aspects of this functional group's appeal. This review is focused on yet another interesting but underappreciated alkyne feature: the fact that the CC alkyne unit has the same oxidation state as the -CH2C(O)- unit of a typical carbonyl compound. Thus, "classic carbonyl chemistry" can be accessed through alkynes, and new transformations can be engineered by unmasking the hidden carbonyl nature of alkynes. The goal of this review is to illustrate the advantages of using alkynes as an entry point to carbonyl reactions while highlighting reports from the literature where, sometimes without full appreciation, the concept of using alkynes as a hidden entry into carbonyl chemistry has been applied.The high energy packed in alkyne functional group makes alkyne reactions highly thermodynamically favorable and generally irreversible. Furthermore, the presence of two orthogonal π-bonds that can be manipulated separately enables flexible synthetic cascades stemming from alkynes. Behind these "obvious" traits, there are other more subtle, often concealed aspects of this functional group's appeal. This review is focused on yet another interesting but underappreciated alkyne feature: the fact that the CC alkyne unit has the same oxidation state as the -CH2C(O)- unit of a typical carbonyl compound. Thus, "classic carbonyl chemistry" can be accessed through alkynes, and new transformations can be engineered by unmasking the hidden carbonyl nature of alkynes. The goal of this review is to illustrate the advantages of using alkynes as an entry point to carbonyl reactions while highlighting reports from the literature where, sometimes without full appreciation, the concept of using alkynes as a hidden entry into carbonyl chemistry has been applied. |
| Author | Alabugin, Igor V. Stepanov, Aleksandr A. Vasilevsky, Sergei F. Kawade, Rahul Kisan Gonzalez-Rodriguez, Edgar |
| AuthorAffiliation | 2 Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Science, 630090 Novosibirsk, Russia; stepanov@kinetics.nsc.ru (A.A.S.); vasilev@kinetics.nsc.ru (S.F.V.) 1 Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306, USA; egonzalez@chem.fsu.edu (E.G.-R.); kawaderahul84@gmail.com (R.K.K.) 3 Novosibirsk State University, 2, Pirogova Str., 630090 Novosibirsk, Russia |
| AuthorAffiliation_xml | – name: 3 Novosibirsk State University, 2, Pirogova Str., 630090 Novosibirsk, Russia – name: 1 Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306, USA; egonzalez@chem.fsu.edu (E.G.-R.); kawaderahul84@gmail.com (R.K.K.) – name: 2 Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Science, 630090 Novosibirsk, Russia; stepanov@kinetics.nsc.ru (A.A.S.); vasilev@kinetics.nsc.ru (S.F.V.) |
| Author_xml | – sequence: 1 givenname: Igor V. orcidid: 0000-0001-9289-3819 surname: Alabugin fullname: Alabugin, Igor V. – sequence: 2 givenname: Edgar surname: Gonzalez-Rodriguez fullname: Gonzalez-Rodriguez, Edgar – sequence: 3 givenname: Rahul Kisan surname: Kawade fullname: Kawade, Rahul Kisan – sequence: 4 givenname: Aleksandr A. surname: Stepanov fullname: Stepanov, Aleksandr A. – sequence: 5 givenname: Sergei F. surname: Vasilevsky fullname: Vasilevsky, Sergei F. |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30875972$$D View this record in MEDLINE/PubMed |
| BookMark | eNp9kk1v1DAQhiNURD_gB3BBlrj0suCv2DEHpNVqoRWVOABna2JPulm8dhsnlfLvcbulaovEydbMM69m3pnj6iCmiFX1ltEPQhj6cZcCuilg5pIqRoV6UR0xyelCUGkOHv0Pq-Oct5RyJln9qjoUtNG10fyogmX4PUfMBDL5Mcdxg2PvyPp66m8gYBwzSR35hmO6Y6Iny-BxM3vMn8iSnPXeYyTrOA4z6eOYyAqGNsU5kNUGd30u8dfVyw5Cxjf370n168v65-pscfH96_lqebFw0ohxUTuptRNGee-MB868qI1i3Jla8hp06xAQWlAt86oBLQxTtEZNBacKAMRJdb7X9Qm29mrodzDMNkFv7wJpuLQwlOECWnBd58C02AkjqVFNUVSNbhy22mCti9bnvdbV1O7Qu2LEAOGJ6NNM7Df2Mt1YJXWxuCkCp_cCQ7qeMI-2mOEwBIiYpmw5M4IpUXNV0PfP0G2ahlissryWhjJZtliod487emjl7yYLwPaAG1LOA3YPCKP29lrsP9dSavSzGtePMPbpdqg-_KfyD1gSx-w |
| CitedBy_id | crossref_primary_10_1016_j_foodchem_2022_133497 crossref_primary_10_1002_anie_202414046 crossref_primary_10_1039_D0OB01718C crossref_primary_10_1002_ajoc_202300360 crossref_primary_10_1021_acscatal_2c06016 crossref_primary_10_1039_D1CS00386K crossref_primary_10_1021_jacs_0c01856 crossref_primary_10_1039_D4CC05546B crossref_primary_10_1016_j_ica_2021_120288 crossref_primary_10_1021_jacs_4c07724 crossref_primary_10_1002_chem_202401027 crossref_primary_10_1016_j_gca_2024_07_013 crossref_primary_10_1070_RCR4902 crossref_primary_10_1021_acs_joc_2c01428 crossref_primary_10_1021_acscatal_4c07259 crossref_primary_10_1021_acs_joc_9b02286 crossref_primary_10_3390_M1252 crossref_primary_10_1070_RCR5020 crossref_primary_10_1039_D0OB00287A crossref_primary_10_1002_ajoc_202000016 crossref_primary_10_1016_j_rser_2021_111103 crossref_primary_10_31857_S0044460X23100013 crossref_primary_10_1021_acs_orglett_3c04057 crossref_primary_10_1134_S1070363223100018 crossref_primary_10_1146_annurev_biochem_032620_110804 crossref_primary_10_1039_D1NJ04736A crossref_primary_10_59761_RCR5145 crossref_primary_10_1021_acs_orglett_1c00381 crossref_primary_10_3390_molecules26102864 crossref_primary_10_1002_anie_202014478 crossref_primary_10_3390_molecules26226883 crossref_primary_10_1021_acs_joc_4c02800 crossref_primary_10_1021_jacs_9b10887 crossref_primary_10_1002_ange_202011472 crossref_primary_10_1002_slct_202000392 crossref_primary_10_1021_acs_orglett_4c02357 crossref_primary_10_1016_j_molstruc_2024_140102 crossref_primary_10_1021_acs_joc_3c02784 crossref_primary_10_1021_acs_orglett_3c03439 crossref_primary_10_1021_acs_joc_1c00388 crossref_primary_10_1021_acs_orglett_4c00172 crossref_primary_10_1038_s41570_023_00479_w crossref_primary_10_1002_ange_202414046 crossref_primary_10_1021_jacs_1c13397 crossref_primary_10_1039_D4OB00530A crossref_primary_10_1002_ange_202014478 crossref_primary_10_1021_acs_joc_2c01638 crossref_primary_10_1002_anie_202011472 crossref_primary_10_1002_chem_202301736 crossref_primary_10_1007_s11172_024_4143_8 crossref_primary_10_1016_j_matchemphys_2020_124019 crossref_primary_10_1021_acs_joc_3c01301 crossref_primary_10_3390_reactions4010002 crossref_primary_10_1021_acs_jafc_0c00835 crossref_primary_10_1016_j_tet_2021_132164 crossref_primary_10_1039_D1OB00193K |
| Cites_doi | 10.1021/jacs.6b11054 10.1002/anie.200601963 10.1021/jo9721251 10.1002/(SICI)1521-3773(19980605)37:10<1415::AID-ANIE1415>3.0.CO;2-N 10.1002/9781118906378 10.1016/j.mencom.2015.09.021 10.1021/ja060369+ 10.1021/cr068430g 10.1016/S0040-4039(02)00082-5 10.1021/jacs.7b06848 10.1021/jo302146r 10.1021/cr030011l 10.1016/j.chempr.2016.06.010 10.1021/ol800539a 10.1021/cr100003s 10.1002/(SICI)1099-0690(199904)1999:4<737::AID-EJOC737>3.0.CO;2-B 10.1021/acs.orglett.6b00585 10.1021/jo034841a 10.1039/c1ra00622c 10.1021/ja043803l 10.1021/ar700234r 10.1021/jo201259j 10.1021/jacs.7b08800 10.1021/ja035729x 10.1002/chem.200204646 10.1021/jo502543b 10.1021/ja075260w 10.1021/ol302922t 10.1021/ja00096a056 10.1021/ja048094q 10.1002/wcms.1261 10.1002/1521-3773(20000818)39:16<2851::AID-ANIE2851>3.0.CO;2-Y 10.1002/anie.201701058 10.1002/anie.201103348 10.1002/1521-3773(20020617)41:12<2132::AID-ANIE2132>3.0.CO;2-S 10.1039/C5SC02402A 10.1021/jo00179a044 10.1038/nchem.131 10.1007/s11172-010-0200-6 10.1021/ja303341b 10.1021/cr100214d 10.1002/anie.201203303 10.1039/jr9520002873 10.1002/anie.201004712 10.1002/chem.201703971 10.1021/ja051689g 10.1002/1521-3765(20020104)8:1<36::AID-CHEM36>3.0.CO;2-L 10.1021/ol050838x 10.1039/C5CS00887E 10.1055/s-1983-30367 10.1002/anie.201606330 10.1021/ar400181x 10.1039/c39760000734 10.1021/cr068435d 10.1039/b816696j 10.1021/jo00373a016 10.1021/jo9008904 10.1021/ol102201z 10.1016/0040-4039(95)02114-0 10.1021/ol0611752 10.1007/BF00963015 10.1002/9783527646869 10.1021/ja052677y 10.1002/poc.2990 10.1002/(SICI)1521-3773(19980518)37:9<1198::AID-ANIE1198>3.0.CO;2-Y 10.1002/anie.201712783 10.1002/wcms.1389 10.3390/molecules24010118 10.1021/ja410424g 10.1039/p29940002141 10.1039/c3cc43872d 10.1016/0040-4020(82)85023-0 10.3762/bjoc.12.162 10.1002/chem.201002918 10.1016/0040-4039(80)80133-X 10.1021/jacs.5b02373 10.1021/ja00415a025 10.1021/ol900142r 10.1021/ja01051a049 10.1039/C6CS00023A 10.1002/jlac.19485600106 10.1021/jo901177e 10.1002/3527605487 10.1021/cr000436x 10.1021/ol052487s 10.1039/C5CC00120J 10.1021/ja0530671 10.1021/jo00122a047 10.1039/b905954g 10.1016/S0040-4039(00)78974-X 10.1038/nchem.331 10.1021/cr500691k 10.1007/BF00929018 10.1021/acs.accounts.7b00385 10.1021/jo102507c 10.1002/anie.201808043 10.1002/anie.201810035 10.1021/jo401091w 10.1002/anie.201103270 10.1021/ja906744r 10.1002/chem.201003096 10.1002/chin.200329088 10.1002/ejoc.201402469 10.1016/j.jfluchem.2016.08.008 10.1021/ja203191f 10.1021/ol900681b 10.1002/anie.201804955 10.1021/cr100347k 10.1016/j.jfluchem.2014.01.019 10.1016/0040-4039(80)80132-8 10.1002/9783527677894 10.1002/poc.3160 10.1039/c39770000233 10.1016/j.tet.2007.04.029 10.1007/BF00950297 10.1021/acs.accounts.8b00026 10.1002/anie.201610374 10.1021/ja0474695 10.1021/jo00011a058 10.1021/jo400699a 10.1002/anie.201609111 10.1021/jo101838a 10.1039/p19790001455 10.1021/ja00018a082 10.1071/CH17026 10.1021/cr00097a015 10.1007/BF00949744 10.1021/jo901551g 10.1021/ja100041e 10.1021/jo01350a045 10.1021/jo00107a012 10.1021/ja906056v 10.1021/ja036410f 10.1002/anie.201604741 10.1021/cr200164y 10.1002/anie.201712651 |
| ContentType | Journal Article |
| Copyright | 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. 2019 by the authors. 2019 |
| Copyright_xml | – notice: 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. – notice: 2019 by the authors. 2019 |
| DBID | AAYXX CITATION NPM 3V. 7X7 7XB 88E 8FI 8FJ 8FK ABUWG AFKRA AZQEC BENPR CCPQU DWQXO FYUFA GHDGH K9. M0S M1P PHGZM PHGZT PIMPY PJZUB PKEHL PPXIY PQEST PQQKQ PQUKI PRINS 7X8 5PM DOA |
| DOI | 10.3390/molecules24061036 |
| DatabaseName | CrossRef PubMed ProQuest Central (Corporate) Health & Medical Collection ProQuest Central (purchase pre-March 2016) Medical Database (Alumni Edition) Hospital Premium Collection Hospital Premium Collection (Alumni Edition) ProQuest Central (Alumni) (purchase pre-March 2016) ProQuest Central (Alumni Edition) ProQuest Central UK/Ireland ProQuest Central Essentials ProQuest Central ProQuest One Community College ProQuest Central Korea Health Research Premium Collection Health Research Premium Collection (Alumni) ProQuest Health & Medical Complete (Alumni) Health & Medical Collection (Alumni Edition) Medical Database ProQuest Central Premium ProQuest One Academic (New) Publicly Available Content Database ProQuest Health & Medical Research Collection ProQuest One Academic Middle East (New) ProQuest One Health & Nursing ProQuest One Academic Eastern Edition (DO NOT USE) ProQuest One Academic ProQuest One Academic UKI Edition ProQuest Central China MEDLINE - Academic PubMed Central (Full Participant titles) DOAJ Directory of Open Access Journals |
| DatabaseTitle | CrossRef PubMed Publicly Available Content Database ProQuest One Academic Middle East (New) ProQuest Central Essentials ProQuest Health & Medical Complete (Alumni) ProQuest Central (Alumni Edition) ProQuest One Community College ProQuest One Health & Nursing ProQuest Central China ProQuest Central ProQuest Health & Medical Research Collection Health Research Premium Collection Health and Medicine Complete (Alumni Edition) ProQuest Central Korea Health & Medical Research Collection ProQuest Central (New) ProQuest Medical Library (Alumni) ProQuest One Academic Eastern Edition ProQuest Hospital Collection Health Research Premium Collection (Alumni) ProQuest Hospital Collection (Alumni) ProQuest Health & Medical Complete ProQuest Medical Library ProQuest One Academic UKI Edition ProQuest One Academic ProQuest One Academic (New) ProQuest Central (Alumni) MEDLINE - Academic |
| DatabaseTitleList | PubMed MEDLINE - Academic CrossRef Publicly Available Content Database |
| Database_xml | – sequence: 1 dbid: DOA name: DOAJ Directory of Open Access Journals url: https://www.doaj.org/ sourceTypes: Open Website – sequence: 2 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 3 dbid: BENPR name: ProQuest Central url: https://www.proquest.com/central sourceTypes: Aggregation Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1420-3049 |
| ExternalDocumentID | oai_doaj_org_article_acffca9bef3940968d686878ceb79e57 PMC6471418 30875972 10_3390_molecules24061036 |
| Genre | Journal Article Review |
| GrantInformation_xml | – fundername: National Science Foundation grantid: CHE-1800329 |
| GroupedDBID | --- 0R~ 123 2WC 53G 5VS 7X7 88E 8FE 8FG 8FH 8FI 8FJ A8Z AADQD AAFWJ AAHBH AAYXX ABDBF ABUWG ACGFO ACIWK ACPRK ACUHS AEGXH AENEX AFKRA AFPKN AFRAH AFZYC AIAGR ALIPV ALMA_UNASSIGNED_HOLDINGS BENPR BPHCQ BVXVI CCPQU CITATION CS3 D1I DIK DU5 E3Z EBD EMOBN ESX FYUFA GROUPED_DOAJ GX1 HH5 HMCUK HYE HZ~ I09 IHR KQ8 LK8 M1P MODMG O-U O9- OK1 P2P PHGZM PHGZT PIMPY PQQKQ PROAC PSQYO RPM SV3 TR2 TUS UKHRP ~8M 3V. ABJCF BBNVY BHPHI HCIFZ KB. M7P M~E NPM PDBOC 7XB 8FK AZQEC DWQXO K9. PJZUB PKEHL PPXIY PQEST PQUKI PRINS 7X8 5PM PUEGO |
| ID | FETCH-LOGICAL-c493t-5c477c396ddc9da21d359612c95425a7bceaeaba6b1d68a7391605e703206aaa3 |
| IEDL.DBID | 7X7 |
| ISSN | 1420-3049 |
| IngestDate | Wed Aug 27 01:30:05 EDT 2025 Thu Aug 21 18:32:44 EDT 2025 Mon Jul 21 09:49:10 EDT 2025 Fri Jul 25 20:04:22 EDT 2025 Wed Feb 19 02:34:11 EST 2025 Thu Apr 24 22:57:54 EDT 2025 Tue Jul 01 03:12:11 EDT 2025 |
| IsDoiOpenAccess | true |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 6 |
| Keywords | cyclizations aldehydes acetals alkynes electronic structure rearrangements catalysis condensations ketones carbonyl compounds nucleophilic addition |
| Language | English |
| License | https://creativecommons.org/licenses/by/4.0 Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-c493t-5c477c396ddc9da21d359612c95425a7bceaeaba6b1d68a7391605e703206aaa3 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 ObjectType-Review-3 content type line 23 |
| ORCID | 0000-0001-9289-3819 |
| OpenAccessLink | https://www.proquest.com/docview/2549014420?pq-origsite=%requestingapplication% |
| PMID | 30875972 |
| PQID | 2549014420 |
| PQPubID | 2032355 |
| ParticipantIDs | doaj_primary_oai_doaj_org_article_acffca9bef3940968d686878ceb79e57 pubmedcentral_primary_oai_pubmedcentral_nih_gov_6471418 proquest_miscellaneous_2193163526 proquest_journals_2549014420 pubmed_primary_30875972 crossref_primary_10_3390_molecules24061036 crossref_citationtrail_10_3390_molecules24061036 |
| ProviderPackageCode | CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 2019-03-15 |
| PublicationDateYYYYMMDD | 2019-03-15 |
| PublicationDate_xml | – month: 03 year: 2019 text: 2019-03-15 day: 15 |
| PublicationDecade | 2010 |
| PublicationPlace | Switzerland |
| PublicationPlace_xml | – name: Switzerland – name: Basel |
| PublicationTitle | Molecules (Basel, Switzerland) |
| PublicationTitleAlternate | Molecules |
| PublicationYear | 2019 |
| Publisher | MDPI AG MDPI |
| Publisher_xml | – name: MDPI AG – name: MDPI |
| References | ref_94 Rautenstrauch (ref_139) 1984; 49 Noyori (ref_107) 1980; 21 Mamane (ref_143) 2004; 126 Liu (ref_88) 2012; 51 Viswanathan (ref_120) 2002; 43 Alabugin (ref_54) 2003; 125 Hashmi (ref_32) 2007; 10 ref_131 ref_133 Balog (ref_116) 1995; 60 Jordan (ref_10) 2016; 1 Vasilevsky (ref_128) 2017; 70 ref_95 Kurtz (ref_115) 2006; 8 Tsvetkov (ref_17) 2018; 57 Jordan (ref_11) 2017; 139 Yaremenko (ref_97) 2016; 12 Rhee (ref_113) 2005; 7 Mukherjee (ref_15) 2009; 74 ref_126 ref_125 Park (ref_30) 2018; 57 Das (ref_25) 2009; 1 Zheng (ref_134) 2016; 45 Scott (ref_9) 1991; 113 Bae (ref_85) 2011; 17 Davydova (ref_129) 2016; 190 Arends (ref_98) 2004; 104 Gade (ref_90) 2016; 18 ref_28 Aaseng (ref_91) 2014; 161 Cui (ref_87) 2010; 49 DeKorver (ref_27) 2010; 110 Dorel (ref_33) 2015; 115 Alabugin (ref_52) 2011; 133 Prikhodko (ref_67) 1990; 39 Beletskaya (ref_29) 2011; 111 Goldfinger (ref_13) 1998; 63 Vasilevsky (ref_70) 2009; 74 ref_79 Harrak (ref_144) 2004; 126 Baldwin (ref_51) 1982; 38 Gomes (ref_101) 2015; 6 Pati (ref_93) 2014; 19 Mesaros (ref_84) 2006; 128 Antoniotti (ref_41) 2005; 127 Palomo (ref_112) 2002; 8 Iborra (ref_61) 1986; 51 Trost (ref_44) 2009; 131 Shi (ref_145) 2005; 127 ref_82 Fox (ref_81) 2008; 41 Umezu (ref_26) 2016; 56 Vasilevsky (ref_127) 2015; 25 Feng (ref_14) 2007; 129 Shvartsberg (ref_64) 1981; 30 Ye (ref_136) 2010; 132 Gilmore (ref_31) 2011; 111 (ref_132) 2004; Volume 13 Yang (ref_20) 2017; 139 Baranov (ref_110) 2011; 1 Goldfinger (ref_12) 1994; 116 Baranov (ref_71) 2010; 59 Cai (ref_78) 2018; 24 Arcadi (ref_34) 2008; 108 Vasilevsky (ref_66) 1981; 30 Baranov (ref_109) 2013; 78 ref_50 Godoi (ref_73) 2011; 111 Trost (ref_111) 1991; Volume 2 Gorin (ref_35) 2008; 108 Alabugin (ref_55) 2005; 127 Padwa (ref_59) 1995; 60 Petasis (ref_80) 1996; 37 Zhang (ref_135) 2014; 47 Strukul (ref_96) 1998; 37 Zeidan (ref_5) 2005; 127 ref_57 Vasilevsky (ref_65) 1978; 30 Cuetos (ref_99) 2011; 50 Smith (ref_83) 2006; 8 Alabugin (ref_4) 2013; 78 Mohamed (ref_16) 2016; 55 Asiri (ref_76) 2016; 45 Perron (ref_38) 1989; 89 Hirano (ref_75) 2011; 76 Roy (ref_124) 2011; 76 Alabugin (ref_48) 2013; 49 Vasilevsky (ref_68) 2012; 25 Marek (ref_24) 2014; 136 Santelli (ref_138) 1983; 6 Gilmore (ref_53) 2012; 134 Mainetti (ref_140) 2002; 41 Miki (ref_141) 2003; 68 Benson (ref_45) 2011; 50 Goodwin (ref_40) 2015; 51 Chernick (ref_1) 2013; 26 Paul (ref_58) 1950; 230 Sze (ref_89) 2011; 17 Crudden (ref_102) 2000; 39 Hein (ref_7) 2017; 50 Pal (ref_146) 2010; 75 Castro (ref_63) 1969; 91 Sperger (ref_122) 2009; 11 Tlais (ref_46) 2010; 12 Gilmore (ref_49) 2016; 6 ref_114 Gomes (ref_105) 2018; 57 ref_117 Saito (ref_119) 2008; 10 Li (ref_47) 2007; 46 ref_118 Trost (ref_123) 2003; 125 Castro (ref_62) 1968; 31 Ozaki (ref_22) 2017; 56 Benitez (ref_137) 2009; 1 Ito (ref_23) 2017; 56 Vasilevsky (ref_72) 2015; 80 Vasilevsky (ref_69) 2009; 74 Kim (ref_86) 2009; 131 ref_39 Druzhinin (ref_130) 2007; 63 Marvell (ref_56) 1980; 21 Criegee (ref_100) 1948; 560 Trost (ref_60) 1981; 103 ref_104 Noyori (ref_106) 1980; 21 ref_103 ref_108 Yang (ref_21) 2018; 57 Teles (ref_43) 1998; 37 Nevado (ref_142) 2003; 9 Alabugin (ref_3) 2018; 51 Dudnik (ref_37) 2010; 43 Mohamed (ref_18) 2015; 137 Gomes (ref_77) 2017; 139 (ref_36) 2009; 38 Byers (ref_74) 2012; 14 ref_2 Fukuda (ref_42) 1991; 56 Yang (ref_19) 2016; 55 Jiang (ref_92) 2013; 78 ref_8 Escalante (ref_121) 2009; 11 ref_6 |
| References_xml | – volume: 139 start-page: 3406 year: 2017 ident: ref_77 article-title: Drawing Catalytic Power from Charge Separation: Stereoelectronic and Zwitterionic Assistance in the Au(I)-Catalyzed Bergman Cyclization publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.6b11054 – ident: ref_117 – volume: 46 start-page: 279 year: 2007 ident: ref_47 article-title: Gold(I)-catalyzed bis-spiroketalization: Synthesis of the trioxadispiroketal-containing A–D rings of Azaspiracid publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.200601963 – volume: 63 start-page: 1676 year: 1998 ident: ref_13 article-title: Synthesis of Ethynyl-Substituted Quinquephenyls and Conversion to Extended Fused-Ring Structures publication-title: J. Org. Chem. doi: 10.1021/jo9721251 – volume: 37 start-page: 1415 year: 1998 ident: ref_43 article-title: Cationic gold(I) complexes: Highly efficient catalysts for the addition of alcohols to alkynes publication-title: Angew. Chem. Int. Ed. doi: 10.1002/(SICI)1521-3773(19980605)37:10<1415::AID-ANIE1415>3.0.CO;2-N – ident: ref_126 doi: 10.1002/9781118906378 – volume: 25 start-page: 377 year: 2015 ident: ref_127 article-title: Reaction of a,b-alkynylketones with b-amino alcohols: Pseudoephedrine assisted cleavage of triple bond via formal internal redox process publication-title: Mendeleev Commun. doi: 10.1016/j.mencom.2015.09.021 – volume: 128 start-page: 5292 year: 2006 ident: ref_84 article-title: Evolution of a Total Synthesis of (−)-Kendomycin Exploiting a Petasis−Ferrier Rearrangement/Ring-Closing Olefin Metathesis Strategy publication-title: J. Am. Chem. Soc. doi: 10.1021/ja060369+ – volume: 108 start-page: 3351 year: 2008 ident: ref_35 article-title: Ligand Effects in Homogeneous Au Catalysis publication-title: Chem. Rev. doi: 10.1021/cr068430g – volume: 43 start-page: 1613 year: 2002 ident: ref_120 article-title: A highly stereoselective, novel coupling reaction between alkynes and aldehydes publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(02)00082-5 – volume: 139 start-page: 13102 year: 2017 ident: ref_20 article-title: Chiral Peropyrene: Synthesis, Structure, and Properties publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.7b06848 – volume: 78 start-page: 2074 year: 2013 ident: ref_109 article-title: Divergent Cyclizations of 1-R-Ethynyl-9,10-anthraquinones: Use of Thiourea as a “S2-” Equivalent in an “Anchor-Relay” Addition Mediated by Formal C-H Activation publication-title: J. Org. Chem. doi: 10.1021/jo302146r – volume: 104 start-page: 4105 year: 2004 ident: ref_98 article-title: The Baeyer−Villiger Reaction: New Developments toward Greener Procedures publication-title: Chem. Rev. doi: 10.1021/cr030011l – ident: ref_39 – volume: 1 start-page: 78 year: 2016 ident: ref_10 article-title: Synthesis of Graphene Nanoribbons via the Topochemical Polymerization and Subsequent Aromatization of a Diacetylene Precursor publication-title: Chem doi: 10.1016/j.chempr.2016.06.010 – volume: 10 start-page: 1783 year: 2008 ident: ref_119 article-title: Novel One-Pot Approach to Synthesis of Indanones through Sb(V)-Catalyzed Reaction of Phenylalkynes with Aldehydes publication-title: Org. Lett. doi: 10.1021/ol800539a – volume: 110 start-page: 5064 year: 2010 ident: ref_27 article-title: Ynamides: A Modern Functional Group for the New Millennium publication-title: Chem. Rev. doi: 10.1021/cr100003s – ident: ref_95 doi: 10.1002/(SICI)1099-0690(199904)1999:4<737::AID-EJOC737>3.0.CO;2-B – ident: ref_108 – volume: 43 start-page: 37 year: 2010 ident: ref_37 article-title: Copper-, Silver-, and Gold Catalyzed Migratory Cycloisomerization Leading to Heterocyclic Five-Membered Rings publication-title: Aldrichim. Acta – volume: 18 start-page: 1844 year: 2016 ident: ref_90 article-title: Gold(I)-Catalyzed Hydroaminaloxylation and Petasis–Ferrier Rearrangement Cascade of Aminaloalkynes publication-title: Org. Lett. doi: 10.1021/acs.orglett.6b00585 – ident: ref_94 – volume: 68 start-page: 8505 year: 2003 ident: ref_141 article-title: Ruthenium-Catalyzed Cyclopropanation of Alkenes Using Propargylic Carboxylates as Precursors of Vinylcarbenoids publication-title: J. Org. Chem. doi: 10.1021/jo034841a – volume: 1 start-page: 1745 year: 2011 ident: ref_110 article-title: Urea as a Solvent and Reagent for the Addition/Cyclization/Fragmentation Cascades Leading to 2-R-7H-dibenzo[de,h]quinolin-7- one Analogues of Aporphinoid Alkaloids publication-title: RSC Adv. doi: 10.1039/c1ra00622c – volume: 127 start-page: 4270 year: 2005 ident: ref_5 article-title: Triplet acetylenes as Synthetic Equivalents of 1,2-Dicarbenes. Phantom n,π* State Controls Reactivity in Triplet Photocycloaddition publication-title: J. Am. Chem. Soc. doi: 10.1021/ja043803l – volume: 41 start-page: 675 year: 2008 ident: ref_81 article-title: Evolution of the Petasis−Ferrier Union/Rearrangement Tactic: Construction of Architecturally Complex Natural Products Possessing the Ubiquitous cis-2,6-Substituted Tetrahydropyran Structural Element publication-title: Acc. Chem. Res. doi: 10.1021/ar700234r – volume: 76 start-page: 7482 year: 2011 ident: ref_124 article-title: Dissecting Alkynes: Full Cleavage of Polarized C≡C Moiety via Sequential Bis-Michael Addition/Retro-Mannich Cascade publication-title: J. Org. Chem. doi: 10.1021/jo201259j – volume: 139 start-page: 15878 year: 2017 ident: ref_11 article-title: Synthesis of N = 8 Armchair Graphene Nanoribbons from Four Distinct Polydiacetylenes publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.7b08800 – volume: 125 start-page: 9329 year: 2003 ident: ref_54 article-title: Control of Kinetics and Thermodynamics of [1,5]-Shifts by Aromaticity: A View Through the Prism of Marcus Theory publication-title: J. Am. Chem. Soc. doi: 10.1021/ja035729x – volume: 9 start-page: 2627 year: 2003 ident: ref_142 article-title: Reaction of Enol Ethers with Alkynes Catalyzed by Transition Metals: 5exo-dig versus 6endo-dig Cyclizations via Cyclopropyl Platinum or Gold Carbene Complexes publication-title: Chem. Eur. J. doi: 10.1002/chem.200204646 – volume: 80 start-page: 1618 year: 2015 ident: ref_72 article-title: Conformational Flexibility of Fused Tetracenedione Propellers Obtained from One-Pot Reductive Dimerization of Acetylenic Quinones publication-title: J. Org. Chem. doi: 10.1021/jo502543b – volume: 129 start-page: 14116 year: 2007 ident: ref_14 article-title: From Helical to Staggered Stacking of Zigzag Nanographenes publication-title: J. Am. Chem. Soc. doi: 10.1021/ja075260w – volume: 14 start-page: 6032 year: 2012 ident: ref_74 article-title: Polyaromatic Ribbon/Benzofuran Fusion via Consecutive Endo Cyclizations of Enediynes publication-title: Org. Lett. doi: 10.1021/ol302922t – volume: 116 start-page: 7895 year: 1994 ident: ref_12 article-title: Fused Polycyclic Aromatics via Electrophile-Induced Cyclization Reactions: Application to the Synthesis of Graphite Ribbons publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00096a056 – volume: 126 start-page: 8654 year: 2004 ident: ref_143 article-title: Platinum- and Gold-Catalyzed Cycloisomerization Reactions of Hydroxylated Enynes publication-title: J. Am. Chem. Soc. doi: 10.1021/ja048094q – volume: 6 start-page: 487 year: 2016 ident: ref_49 article-title: The Baldwin Rules: Revised and Extended publication-title: WIREs Comput. Mol. Sci. doi: 10.1002/wcms.1261 – volume: 39 start-page: 2851 year: 2000 ident: ref_102 article-title: A Demonstration of the Primary Stereoelectronic Effect in the Baeyer–Villiger Oxidation of α-Fluorocyclohexanones publication-title: Angew. Chem. Int. Ed. doi: 10.1002/1521-3773(20000818)39:16<2851::AID-ANIE2851>3.0.CO;2-Y – volume: 56 start-page: 11144 year: 2017 ident: ref_23 article-title: Annulative π-Extension (APEX): Rapid Access to Fused Arenes, Heteroarenes, and Nanographenes publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201701058 – volume: 50 start-page: 8387 year: 2011 ident: ref_99 article-title: Dynamic Kinetic Resolution of α-Substituted β-Ketoesters Catalyzed by Baeyer–Villiger Monooxygenases: Access to Enantiopure α-Hydroxy Esters publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201103348 – volume: 41 start-page: 2132 year: 2002 ident: ref_140 article-title: The Effect of a Hydroxy Protecting Group on the PtCl2-Catalyzed Cyclization of Dienynes—A Novel, Efficient, and Selective Synthesis of Carbocycles publication-title: Angew. Chem. Int. Ed. doi: 10.1002/1521-3773(20020617)41:12<2132::AID-ANIE2132>3.0.CO;2-S – volume: 6 start-page: 6783 year: 2015 ident: ref_101 article-title: Stereoelectronic source of the anomalous stability of bis-peroxides publication-title: Chem. Sci. doi: 10.1039/C5SC02402A – volume: 49 start-page: 950 year: 1984 ident: ref_139 article-title: 2-Cyclopentenones from 1-ethynyl-2-propenyl acetates publication-title: J. Org. Chem. doi: 10.1021/jo00179a044 – volume: 1 start-page: 128 year: 2009 ident: ref_25 article-title: A unique approach to aldol products for the creation of all-carbon quaternary stereocentres publication-title: Nat. Chem. doi: 10.1038/nchem.131 – volume: 59 start-page: 1031 year: 2010 ident: ref_71 article-title: Reaction of guanidine with peri-substituted (R-ethynyl)-9,10-anthraquinones bearing electron-donating substituents publication-title: Russ. Chem. Bull. doi: 10.1007/s11172-010-0200-6 – volume: 134 start-page: 10584 year: 2012 ident: ref_53 article-title: Aromatic Transition States in Non-Pericyclic Reactions: Anionic 5-Endo Cyclizations are Aborted Sigmatropic Shifts publication-title: J. Amer. Chem. Soc. doi: 10.1021/ja303341b – volume: 111 start-page: 2937 year: 2011 ident: ref_73 article-title: Synthesis of Heterocycles via Electrophilic Cyclization of Alkynes Containing Heteroatom publication-title: Chem. Rev. doi: 10.1021/cr100214d – volume: 51 start-page: 7301 year: 2012 ident: ref_88 article-title: Access to Electron-Rich Arene-Fused Hexahydroquinolizinones through a Gold-Catalysis-Initiated Cascade Process publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201203303 – ident: ref_57 doi: 10.1039/jr9520002873 – volume: 49 start-page: 9178 year: 2010 ident: ref_87 article-title: A Modular, Efficient, and Stereoselective Synthesis of Substituted Piperidin-4-ols publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201004712 – volume: 24 start-page: 1606 year: 2018 ident: ref_78 article-title: Efficient endo Cycloisomerization of Terminal Alkynols Catalyzed by a New Ruthenium Complex with 8-(Diphenylphosphino)quinoline Ligand and Mechanistic Investigation publication-title: Chem. Eur. J. doi: 10.1002/chem.201703971 – volume: 127 start-page: 5802 year: 2005 ident: ref_145 article-title: Synthesis of 2-Cyclopentenones by Gold(I)-Catalyzed Rautenstrauch Rearrangement publication-title: J. Am. Chem. Soc. doi: 10.1021/ja051689g – volume: 8 start-page: 36 year: 2002 ident: ref_112 article-title: The Aldol Addition Reaction: An Old Transformation at Constant Rebirth publication-title: Chem. Eur. J. doi: 10.1002/1521-3765(20020104)8:1<36::AID-CHEM36>3.0.CO;2-L – volume: 7 start-page: 2493 year: 2005 ident: ref_113 article-title: Alkynes as Synthetic Equivalents to Stabilized Wittig Reagents: Intra- and Intermolecular Carbonyl Olefinations Catalyzed by Ag(I), BF3, and HBF4 publication-title: Org. Lett. doi: 10.1021/ol050838x – volume: 45 start-page: 4448 year: 2016 ident: ref_134 article-title: Au-Catalysed oxidative cyclisation publication-title: Chem. Soc. Rev. doi: 10.1039/C5CS00887E – volume: 6 start-page: 429 year: 1983 ident: ref_138 article-title: The Nazarov Cyclisation publication-title: Synthesis doi: 10.1055/s-1983-30367 – volume: 55 start-page: 12054 year: 2016 ident: ref_16 article-title: Alkynes as Linchpins for the Additive Annulation of Biphenyls: Convergent Construction of Functionalized Fused Helicenes publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201606330 – volume: 47 start-page: 877 year: 2014 ident: ref_135 article-title: A non-diazo approach to α-oxo gold carbenes via gold-catalyzed alkyne oxidation publication-title: Acc. Chem. Res. doi: 10.1021/ar400181x – ident: ref_125 doi: 10.1039/c39760000734 – volume: 108 start-page: 3266 year: 2008 ident: ref_34 article-title: Alternative Synthetic Methods Through New Developments in Catalysis by Gold publication-title: Chem. Rev. doi: 10.1021/cr068435d – volume: 38 start-page: 3208 year: 2009 ident: ref_36 article-title: Gold and platinum catalysis-a convenient tool for generating molecular complexity publication-title: Chem. Soc. Rev. doi: 10.1039/b816696j – volume: 51 start-page: 4432 year: 1986 ident: ref_61 article-title: 6-Endo-Dig vs. 5-Exo-Dig ring closure in o-hydroxyaryl phenylethynyl ketones. A new approach to the synthesis of flavones and aurones publication-title: J. Org. Chem. doi: 10.1021/jo00373a016 – volume: 74 start-page: 6143 year: 2009 ident: ref_70 article-title: An Unexpected Rearrangement which Disassembles Alkyne Moiety Through Formal Nitrogen Atom Insertion between Two Acetylenic Carbons and Related Cascade Transformations: New Approach to Sampagine Derivatives and Polycyclic Aromatic Amides publication-title: J. Org. Chem. doi: 10.1021/jo9008904 – volume: 12 start-page: 4698 year: 2010 ident: ref_46 article-title: Stereocontrol of 5,5-spiroketals in the synthesis of Cephalosporolide H epimers publication-title: Org. Lett. doi: 10.1021/ol102201z – volume: 37 start-page: 141 year: 1996 ident: ref_80 article-title: STEREOCONTROLLED SYNTHESIS OF SUBSTITUTED TETRAHYDROPYRANS FROM 1,3-DIOXAN-4-ONES publication-title: Tetrahedron Lett. doi: 10.1016/0040-4039(95)02114-0 – volume: 8 start-page: 3315 year: 2006 ident: ref_83 article-title: Total Synthesis of the Marine Natural Product (−)-Clavosolide, A. A Showcase for the Petasis—Ferrier Union/Rearrangement Tactic publication-title: Org. Lett. doi: 10.1021/ol0611752 – volume: 39 start-page: 120 year: 1990 ident: ref_67 article-title: Synthesis and certain properties of acetylenylindoles publication-title: Russ. Chem. Bull. doi: 10.1007/BF00963015 – ident: ref_133 doi: 10.1002/9783527646869 – volume: 127 start-page: 12583 year: 2005 ident: ref_55 article-title: Thermodynamic and Strain Effects in the Competition Between 5-Exo-dig and 6-Endo-Dig Cyclizations of Vinyl and Aryl Radicals publication-title: J. Am. Chem. Soc. doi: 10.1021/ja052677y – volume: 25 start-page: 998 year: 2012 ident: ref_68 article-title: Strain Control in Nucleophilic Cyclizations: Reversal of exo-Selectivity in Cyclizations of Hydrazides of Acetylenyl Carboxylic Acids by Annealing to a Pyrazole Scaffold publication-title: J. Phys. Org. Chem. doi: 10.1002/poc.2990 – volume: 37 start-page: 1198 year: 1998 ident: ref_96 article-title: Transition Metal Catalysis in the Baeyer–Villiger Oxidation of Ketones publication-title: Angew. Chem. Int. Ed. doi: 10.1002/(SICI)1521-3773(19980518)37:9<1198::AID-ANIE1198>3.0.CO;2-Y – volume: 57 start-page: 3651 year: 2018 ident: ref_17 article-title: Radical Alkyne Peri-annulations for Synthesis of Functionalized Phenalenes, Benzanthrenes, and Olympicene publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201712783 – ident: ref_104 doi: 10.1002/wcms.1389 – ident: ref_6 doi: 10.3390/molecules24010118 – volume: 136 start-page: 2682 year: 2014 ident: ref_24 article-title: All-Carbon Quaternary Stereogenic Centers in Acyclic Systems through the Creation of Several C–C Bonds per Chemical Step publication-title: J. Am. Chem. Soc. doi: 10.1021/ja410424g – ident: ref_103 doi: 10.1039/p29940002141 – volume: 49 start-page: 11246 year: 2013 ident: ref_48 article-title: Finding the right path: Baldwin “Rules for Ring Closure” and stereoelectronic control of cyclizations. (Invited “Viewpoint”) publication-title: Chem. Commun. doi: 10.1039/c3cc43872d – volume: 38 start-page: 2939 year: 1982 ident: ref_51 article-title: Rules for ring closure: Application to intramolecular aldol condensations in polyketonic substrates publication-title: Tetrahedron doi: 10.1016/0040-4020(82)85023-0 – volume: 12 start-page: 1647 year: 2016 ident: ref_97 article-title: Rearrangements of organic peroxides and related processes publication-title: Beilstein J. Org. Chem. doi: 10.3762/bjoc.12.162 – volume: 17 start-page: 1433 year: 2011 ident: ref_85 article-title: Gold(I)-Catalyzed Access to Tetrahydropyran-4-ones from 4 (Alkoxyalkyl)oxy-1-butynes: Formal Catalytic Petasis–Ferrier Rearrangement publication-title: Chem. Eur. J. doi: 10.1002/chem.201002918 – volume: 21 start-page: 2573 year: 1980 ident: ref_107 article-title: Remote substituent effects in the Baeyer-Villiger oxidation. II. regioselection based on the hydroxyl group orientation in the tetrahedral intermediate publication-title: Tetrahedron Lett. doi: 10.1016/0040-4039(80)80133-X – volume: 137 start-page: 6335 year: 2015 ident: ref_18 article-title: Alkenes as Alkyne Equivalents in Radical Cascades Terminated by Fragmentations: Overcoming Stereoelectronic Restrictions on Ring Expansions for the Preparation of Expanded Polyaromatics publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.5b02373 – volume: 103 start-page: 7559 year: 1981 ident: ref_60 article-title: Palladium-catalyzed 1,3-oxygen-to-carbon alkyl shifts. A cyclopentanone synthesis publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00415a025 – volume: 11 start-page: 1531 year: 2009 ident: ref_121 article-title: Brønsted Acid-Promoted Intramolecular Carbocyclization of Alkynals Leading to Cyclic Enones publication-title: Org. Lett. doi: 10.1021/ol900142r – volume: 91 start-page: 6464 year: 1969 ident: ref_63 article-title: Copper(I) substitutions. Scope and mechanism of cuprous acetylide substitutions publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01051a049 – volume: 45 start-page: 4471 year: 2016 ident: ref_76 article-title: Gold-catalysed reactions of diynes publication-title: Chem. Soc. Rev. doi: 10.1039/C6CS00023A – volume: 560 start-page: 127 year: 1948 ident: ref_100 article-title: Die Umlagerung der Dekalin-peroxydester als Folge von kationischem Sauerstoff publication-title: Justus Liebigs Ann. Chem. doi: 10.1002/jlac.19485600106 – volume: Volume 2 start-page: 99 year: 1991 ident: ref_111 article-title: The Aldol Reactions publication-title: Comprehensive Organic Synthesis – volume: 74 start-page: 6311 year: 2009 ident: ref_15 article-title: A Convenient Synthesis of Tetrabenzo-[de,hi,mn,qr]naphthacene from Readily Available 1,2-Di(phenanthren4-yl)ethyne publication-title: J. Org. Chem. doi: 10.1021/jo901177e – ident: ref_2 doi: 10.1002/3527605487 – volume: 10 start-page: 3180 year: 2007 ident: ref_32 article-title: Gold-Catalyzed Organic Reactions publication-title: Chem. Rev. doi: 10.1021/cr000436x – volume: 8 start-page: 231 year: 2006 ident: ref_115 article-title: A Ring-Closing Yne-Carbonyl Metathesis of Ynamides publication-title: Org. Lett. doi: 10.1021/ol052487s – volume: 51 start-page: 8730 year: 2015 ident: ref_40 article-title: Regioselectivity in the Au-catalyzed hydration and hydroalkoxylation of alkynes publication-title: Chem. Commun. doi: 10.1039/C5CC00120J – volume: 127 start-page: 9976 year: 2005 ident: ref_41 article-title: Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0530671 – volume: 60 start-page: 5595 year: 1995 ident: ref_59 article-title: An Unusual Example of a 6-Endo-Dig Addition to an Unactivated Carbon-Carbon Triple Bond publication-title: J. Org. Chem. doi: 10.1021/jo00122a047 – ident: ref_114 doi: 10.1039/b905954g – volume: 21 start-page: 2123 year: 1980 ident: ref_56 article-title: A novel synthesis of 4-cycloheptenones publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)78974-X – volume: 1 start-page: 482 year: 2009 ident: ref_137 article-title: A Bonding Model for Gold(I) Carbene Complexes publication-title: Nat. Chem. doi: 10.1038/nchem.331 – volume: 115 start-page: 9028 year: 2015 ident: ref_33 article-title: Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity publication-title: Chem. Rev. doi: 10.1021/cr500691k – volume: 30 start-page: 1021 year: 1978 ident: ref_65 article-title: Condensation of N-methyl-4-iodopyra zolecarboxylic acids with copper acetylides publication-title: Russ. Chem. Bull. doi: 10.1007/BF00929018 – volume: 50 start-page: 2776 year: 2017 ident: ref_7 article-title: Alkyne Benzannulation Reactions for the Synthesis of Novel Aromatic Architectures publication-title: Acc. Chem. Res. doi: 10.1021/acs.accounts.7b00385 – volume: 76 start-page: 1212 year: 2011 ident: ref_75 article-title: Direct Synthesis of Fused Indoles by Gold-Catalyzed Cascade Cyclization of Diynes publication-title: J. Org. Chem. doi: 10.1021/jo102507c – volume: 57 start-page: 14773 year: 2018 ident: ref_21 article-title: Highly Regioselective Domino Benzannulation Reaction of Buta-1,3-diynes to Construct Irregular Nanographenes publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201808043 – ident: ref_28 doi: 10.1002/anie.201810035 – volume: 78 start-page: 7777 year: 2013 ident: ref_4 article-title: “Two Functional Groups in One Package”: Using Both Alkyne π-Bonds in Cascade Transformations publication-title: J. Org. Chem. doi: 10.1021/jo401091w – volume: 50 start-page: 8739 year: 2011 ident: ref_45 article-title: Second-generation total synthesis of Spirastrellolide F methyl ester: The alkyne route publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201103270 – volume: 131 start-page: 14660 year: 2009 ident: ref_86 article-title: Formal Alkyne Aza-Prins Cyclization: Gold(I)-Catalyzed Cycloisomerization of Mixed N,O-Acetals Generated from Homopropargylic Amines to Highly Substituted Piperidines publication-title: J. Am. Chem. Soc. doi: 10.1021/ja906744r – volume: Volume 13 start-page: 59 year: 2004 ident: ref_132 article-title: Metal Carbenes in Organic Synthesis publication-title: Topics in Organometallic Chemistry – volume: 17 start-page: 1437 year: 2011 ident: ref_89 article-title: Gold-Catalyzed Tandem Intramolecular Heterocyclization/Petasis–Ferrier Rearrangement of 2-(Prop-2-ynyloxy)benzaldehydes as an Expedient Route to Benzo[b]oxepin-3(2 H)-ones publication-title: Chem. Eur. J. doi: 10.1002/chem.201003096 – ident: ref_118 doi: 10.1002/chin.200329088 – volume: 19 start-page: 3986 year: 2014 ident: ref_93 article-title: Synthesis of Substituted Biaryls Through Gold-Catalyzed Petasis-Ferrier Rearrangement of Propargyl Ethers publication-title: Eur. J. Org. Chem. doi: 10.1002/ejoc.201402469 – volume: 190 start-page: 61 year: 2016 ident: ref_129 article-title: Reaction of trifluoroacetyl acetylenes with β-amino alcohols. Synthesis of enaminoketones and unusual fragmentation publication-title: J. Fluorine Chem. doi: 10.1016/j.jfluchem.2016.08.008 – ident: ref_131 – volume: 133 start-page: 12608 year: 2011 ident: ref_52 article-title: Rules for Anionic and Radical Ring Closure of Alkynes publication-title: J. Am. Chem. Soc. doi: 10.1021/ja203191f – volume: 11 start-page: 2449 year: 2009 ident: ref_122 article-title: Gold-Catalyzed Cyclizations of 1,6-Diynes publication-title: Org. Lett. doi: 10.1021/ol900681b – volume: 57 start-page: 13598 year: 2018 ident: ref_30 article-title: Catalytic Alkyne Arylation Using Traceless Directing Groups publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201804955 – volume: 111 start-page: 1596 year: 2011 ident: ref_29 article-title: Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions publication-title: Chem. Rev. doi: 10.1021/cr100347k – volume: 161 start-page: 142 year: 2014 ident: ref_91 article-title: 3-Fluorotetrahydropyran-4-one derivatives from homopropargyl acetal publication-title: J. Fluorine Chem. doi: 10.1016/j.jfluchem.2014.01.019 – volume: 21 start-page: 2569 year: 1980 ident: ref_106 article-title: Remote substituent effects in the Baeyer-Villiger oxidation. I. through-bond γ substituent effect on the regioselectivity publication-title: Tetrahedron Lett. doi: 10.1016/0040-4039(80)80132-8 – ident: ref_8 doi: 10.1002/9783527677894 – volume: 26 start-page: 742 year: 2013 ident: ref_1 article-title: Carbon-rich nanostructures: The conversion of acetylenes into materials publication-title: J. Phys. Org. Chem. doi: 10.1002/poc.3160 – ident: ref_50 doi: 10.1039/c39770000233 – volume: 63 start-page: 7753 year: 2007 ident: ref_130 article-title: Recent advances in the chemistry of α,β-unsaturated trifluoromethylketones publication-title: Tetrahedron doi: 10.1016/j.tet.2007.04.029 – ident: ref_82 – volume: 30 start-page: 1071 year: 1981 ident: ref_64 article-title: Cyclization of acetylenylpyrazolecarboxylic acids publication-title: Russ. Chem. Bull. doi: 10.1007/BF00950297 – volume: 51 start-page: 1206 year: 2018 ident: ref_3 article-title: Alkyne Origami: Folding Oligoalkynes into Polyaromatics publication-title: Acc. Chem. Res. doi: 10.1021/acs.accounts.8b00026 – volume: 56 start-page: 1361 year: 2017 ident: ref_22 article-title: One-Step Annulative π-Extension of Alkynes with Dibenzosiloles or Dibenzogermoles by Palladium/o-chloranil Catalysis publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201610374 – volume: 126 start-page: 8656 year: 2004 ident: ref_144 article-title: PtCl2-Catalyzed Cycloisomerizations of 5-En-1-yn-3-ol Systems publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0474695 – volume: 56 start-page: 3729 year: 1991 ident: ref_42 article-title: Effective transformation of unactivated alkynes into ketones or acetals with a gold(III) catalyst publication-title: J. Org. Chem. doi: 10.1021/jo00011a058 – volume: 78 start-page: 6947 year: 2013 ident: ref_92 article-title: DFT Study on the Mechanism and Stereochemistry of the Petasis–Ferrier Rearrangements publication-title: J. Org. Chem. doi: 10.1021/jo400699a – volume: 56 start-page: 1298 year: 2016 ident: ref_26 article-title: Regioselective One-Pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201609111 – volume: 75 start-page: 8689 year: 2010 ident: ref_146 article-title: Fast Oxy-Cope Rearrangements of Bis-alkynes: Competition with Central C−C Bond Fragmentation and Incorporation in Tunable Cascades Diverging from a Common Bis-allenic Intermediate publication-title: J. Org. Chem. doi: 10.1021/jo101838a – ident: ref_79 doi: 10.1039/p19790001455 – volume: 113 start-page: 7082 year: 1991 ident: ref_9 article-title: Corannulene. A convenient new synthesis publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00018a082 – volume: 70 start-page: 421 year: 2017 ident: ref_128 article-title: Full Cleavage of C≡C Bond in Electron-Deficient Acetylenes via Reaction with Ethylenediamine publication-title: Aust. J. Chem. doi: 10.1071/CH17026 – volume: 89 start-page: 1617 year: 1989 ident: ref_38 article-title: Chemistry of spiroketals publication-title: Chem. Rev. doi: 10.1021/cr00097a015 – volume: 230 start-page: 1872 year: 1950 ident: ref_58 article-title: Derivatives of 4-pentyn-1-ol publication-title: C. R. Acad. Sci. – volume: 30 start-page: 683 year: 1981 ident: ref_66 article-title: Condensation of iodo-N-methylpyrazole-4-carboxylic acids with copper acetylides publication-title: Russ. Chem. Bull. doi: 10.1007/BF00949744 – volume: 74 start-page: 8106 year: 2009 ident: ref_69 article-title: Tuning Selectivity of Anionic Cyclizations: Competition between 5-Exo- and 6-Endo-dig Closures of Hydrazides of o-Acetylenyl Benzoic Acids and Based-catalyzed Fragmentation/Recyclization of the Initial 5-Exo-Dig Products publication-title: J. Org. Chem. doi: 10.1021/jo901551g – volume: 132 start-page: 3258 year: 2010 ident: ref_136 article-title: Alkynes as Equivalents of α-Diazo Ketones in Generating α-Oxo Metal Carbenes: A Gold-Catalyzed Expedient Synthesis of Dihydrofuran-3-ones publication-title: J. Am. Chem. Soc. doi: 10.1021/ja100041e – volume: 31 start-page: 4071 year: 1968 ident: ref_62 article-title: Indoles, Benzofurans, Phthalides, and Tolanes via Copper(I) Acetylides publication-title: J. Org. Chem. doi: 10.1021/jo01350a045 – volume: 60 start-page: 345 year: 1995 ident: ref_116 article-title: Additive and Medium Effects on Lewis Acid-Promoted Cationic.pi.-Cyclizations of Alkenyl- and Alkynylcyclopentane-1,3-diones publication-title: J. Org. Chem. doi: 10.1021/jo00107a012 – volume: 131 start-page: 15061 year: 2009 ident: ref_44 article-title: Total Synthesis and Stereochemical Assignment of (−)-Ushikulide, A publication-title: J. Am. Chem. Soc. doi: 10.1021/ja906056v – volume: 125 start-page: 11516 year: 2003 ident: ref_123 article-title: A Mechanistic Dichotomy in Ruthenium-Catalyzed Propargyl Alcohol Reactivity: A Novel Hydrative Diyne Cyclization publication-title: J. Am. Chem. Soc. doi: 10.1021/ja036410f – volume: 55 start-page: 10427 year: 2016 ident: ref_19 article-title: Pyrenes, Peropyrenes, and Teropyrenes: Synthesis, Structures, and Photophysical Properties publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201604741 – volume: 111 start-page: 6513 year: 2011 ident: ref_31 article-title: Cyclizations of Alkynes: Revisiting Baldwin’s Rules for Ring Closure publication-title: Chem. Rev. doi: 10.1021/cr200164y – volume: 57 start-page: 3372 year: 2018 ident: ref_105 article-title: Interrupted Baeyer–Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201712651 |
| SSID | ssj0021415 |
| Score | 2.4844792 |
| SecondaryResourceType | review_article |
| Snippet | The high energy packed in alkyne functional group makes alkyne reactions highly thermodynamically favorable and generally irreversible. Furthermore, the... |
| SourceID | doaj pubmedcentral proquest pubmed crossref |
| SourceType | Open Website Open Access Repository Aggregation Database Index Database Enrichment Source |
| StartPage | 1036 |
| SubjectTerms | acetals aldehydes alkynes carbonyl compounds catalysis Chemistry condensations cyclizations electronic structure Energy Hydration ketones nucleophilic addition Oxidation rearrangements Review |
| SummonAdditionalLinks | – databaseName: DOAJ Directory of Open Access Journals dbid: DOA link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV1Lb9NAEF6hXuCCgPIwFLSVOCFZteN9eHsLUaoIVC5QqTdrdnesRgSnNMkh_74ztmMaQOXCzfKO5fHsrOcb7ew3QrzHmmK08pgqhy6la5N6pfMUTdSxCGXtPZ9GPv9iZhfq06W-vNPqi2vCOnrgznAnEOo6gPNYcw9vZ8poSlPaMqC3DnV7jpxi3i6Z6lOtnOJSt4dZUFJ_8qNrNYurNn5lLR_zryjUkvX_DWH-Xih5J_KcPRGPe8gox52qT8UDbJ6Jh5Ndp7ZDAePF9y39siSs5NdtQ5COJOX052ZObsSFEnJZy8_ItNsk00Q5XkS82kZcncqxnDGJSCOn3GFEzpv1Uk7gxnPBuhze8VxcnE2_TWZp3zohDcoV61QHZW0onIkxuAijPBbaEZgJTtMiBesDAoIH43OyJ1g-fptptNxO3QBA8UIcNKTVKyEJPygssqiA0EZ0xkX0PgDPhS1NwERkO1NWoecV5_YWi4ryC7Z-9Yf1E_FheOS6I9W4T_gjz88gyHzY7Q3ykqr3kupfXpKIo93sVv0iXVWcG3NCOcoScTwMk115zwQaXG5IhgAuQVY9Ij1eds4waMJkipSPjRJh99xkT9X9kWZ-1VJ4G8IEKi9f_49veyMeEYpzXBiX6yNxsL7Z4FtCSmv_rl0Ut2OAFnc priority: 102 providerName: Directory of Open Access Journals |
| Title | Alkynes as Synthetic Equivalents of Ketones and Aldehydes: A Hidden Entry into Carbonyl Chemistry |
| URI | https://www.ncbi.nlm.nih.gov/pubmed/30875972 https://www.proquest.com/docview/2549014420 https://www.proquest.com/docview/2193163526 https://pubmed.ncbi.nlm.nih.gov/PMC6471418 https://doaj.org/article/acffca9bef3940968d686878ceb79e57 |
| Volume | 24 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV1Lj9MwELZg9wAXxJvAUhmJE1K0SRPbMRfUrVoqECsErNRb5Mdkt6Iku0176L9nJklTCmgvUZRMlIk99nxjT75h7C0U6KNTC2GqQYd4LkObijgE6YVPXFZYS38jfzmXs4v001zMuwW3ukur3M2JzUTtK0dr5KcUyBD6H0Yfrm9CqhpFu6tdCY277JioyyilS833AVeM3qndyUwwtD_91RachbrxYlHDyrz3RQ1l__9w5t_pkn_4n-lD9qADjnzU9vQjdgfKx-zeeFev7Qkzo-XPLU5c3NT8-7ZEYIeSfHKzWaAxUboErwr-GYh8G2VKz0dLD1dbD_V7PuIzohIp-YTqjPBFua742Kwspa3z_h1P2cV08mM8C7sCCqFLdbIOhUuVcomW3jvtzTD2idAIaZwWOFSNsg4MGGukjb3MjKKfcCMBioqqS2NM8owdlajVC8YRRaSQRD41iDm8ltqDtc5gdIjeTjoIWLRrytx17OJU5GKZY5RBrZ__0_oBe9c_ct1Sa9wmfEb90wsSK3ZzoVpd5t0gy40rCme0hYLqvWuZ4VfJTGUOrNIgVMBOdr2bd0O1zveGFbA3_W1sV9o5MSVUG5RBmIvAVQxRj-etMfSaEKUiRmXDgKkDMzlQ9fBOubhqiLwlIoM0zl7ertYrdh9RmqbEt1icsKP1agOvEQmt7aAxdzxm048Ddnw2Of_6bdCsKvwG08sQLw |
| linkProvider | ProQuest |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwtV1Lb9NAEF6VcigXxBtDgUWCC5JVP9deJIRCSEhJ2wut1JvZx5hGBLuNE6H8KX4jM36VAOqtt8g7diaz451vsrPzMfYKcozRkQY3kiBd_CxcHcW-C8LGNjRprjWdRj48EpOT6PNpfLrFfnVnYaisslsT64Xalob-I9-jRIbQf-C9P79wiTWKdlc7Co3GLaaw_okpW_Vu_yPO7-sgGI-OhxO3ZRVwTSTDpRubKElMKIW1RloV-DaMJcZ5I2P0X5VoAwqUVkL7VqQqoZOpXgwJMY0LpVSIz73BbkYhPoJOpo8_9Qmej9Gw2TnFQW_vR0NwC1UdNb26C_Rl7KspAv6Ha_8uz_wj3o3vsNstUOWDxrPusi0o7rGdYccPd5-pwfz7GhdKrir-ZV0gkERJPrpYzdB5qTyDlzmfAjX7RpnC8sHcwtnaQvWWD_iEWpcUfES8JnxWLEs-VAtNZfK8_44H7ORaTPuQbReo1WPGEbVEEHo2UohxrBTSgtZGYTaK0VUYcJjXmTIzbTdzItWYZ5jVkPWzf6zvsDf9LedNK4-rhD_Q_PSC1IW7vlAuvmXtS50pk-dGSQ058ctLkeKvEmmSGtCJhDhx2G43u1m7NFTZpSM77GU_jHalnRpVQLlCGYTVCJTjAPV41DhDrwm1cMQsMHBYsuEmG6pujhSzs7pxuEAkEvnpk6vVesF2JseHB9nB_tH0KbuFCFFS0Z0f77Lt5WIFzxCFLfXz2vU5-3rd79pvVnZJrA |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwtV1Lj9MwELaWRQIuiDeFBYwEF6SoedmOkRAq3VZdCiskWKm34FfYipLsNq1Q_xq_jpm8SgHtbW9VMk2n47Hnm3g8HyEvXAYxOtbOi6WTHnzmno5Z4DlumY1MkmmNp5E_HvPJSfx-xmZ75Fd7FgbLKts1sVqobWHwHXkfExlE_6Hfz5qyiE-H47dn5x4ySOFOa0unUbvI1G1-QvpWvjk6hLF-GYbj0ZfhxGsYBjwTy2jlMRMLYSLJrTXSqjCwEZMQ841k4MtKaOOUU1pxHVieKIGnVH3mBLKOc6VUBM-9Qq6KiAU4x8Rsm-wFEBnrXdQokn7_R01268oqgvpVR-htHKzoAv6Hcf8u1fwj9o1vkZsNaKWD2stukz2X3yHXhy1X3F2iBovvG1g0qSrp500OoBIk6eh8PQdHxlINWmR06rDxN8jklg4W1p1urCtf0wGdYBuTnI6Q44TO81VBh2qpsWSedr9xj5xcimnvk_0ctHpIKCCY2EW-jRXgHSu5tE5royAzhUjLjesRvzVlaprO5kiwsUghw0Hrp_9Yv0dedV85q9t6XCT8DsenE8SO3NWFYvktbSZ4qkyWGSW1y5BrXvIE_hVPRGKcFtIx0SMH7eimzTJRplun7pHn3W2wK-7aqNwVa5ABiA2gmYWgx4PaGTpNsJ0jZIRhj4gdN9lRdfdOPj-tmohzQCVxkDy6WK1n5BrMsvTD0fH0MbkBYFFi_V3ADsj-arl2TwCQrfTTyvMp-XrZU-03QqZN2Q |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Alkynes+as+Synthetic+Equivalents+of+Ketones+and+Aldehydes%3A+A+Hidden+Entry+into+Carbonyl+Chemistry&rft.jtitle=Molecules+%28Basel%2C+Switzerland%29&rft.au=Alabugin%2C+Igor+V&rft.au=Gonzalez-Rodriguez%2C+Edgar&rft.au=Kawade%2C+Rahul+Kisan&rft.au=Stepanov%2C+Aleksandr+A&rft.date=2019-03-15&rft.pub=MDPI+AG&rft.eissn=1420-3049&rft.volume=24&rft.issue=6&rft.spage=1036&rft_id=info:doi/10.3390%2Fmolecules24061036&rft.externalDBID=HAS_PDF_LINK |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1420-3049&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1420-3049&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1420-3049&client=summon |