1,4-Hydroboration Reactions of Electron-Poor Aromatic Rings by N‑Heterocyclic Carbene Boranes
Reactions of N-heterocyclic carbene boranes (NHC-boranes) with electron-poor aromatic rings under photoredox conditions provide dearomatized 3-NHC-boryl-1,5-cycohexadienes, which are formally products of 1,4-hydroboration reactions. When regioisomers are possible, the more crowded (doubly ortho-subs...
Saved in:
Published in | Journal of the American Chemical Society Vol. 142; no. 13; pp. 6261 - 6267 |
---|---|
Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
01.04.2020
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | Reactions of N-heterocyclic carbene boranes (NHC-boranes) with electron-poor aromatic rings under photoredox conditions provide dearomatized 3-NHC-boryl-1,5-cycohexadienes, which are formally products of 1,4-hydroboration reactions. When regioisomers are possible, the more crowded (doubly ortho-substituted) product is formed preferably or exclusively. The mechanism may involve oxidation of the NHC-borane to an NHC-boryl radical, reduction of the electron-poor aromatic ring to a radical anion, coupling of the radical and the radical anion to give a cyclohexadienyl anion, and finally regioselective protonation. |
---|---|
AbstractList | Reactions of N-heterocyclic carbene boranes (NHC-boranes) with electron-poor aromatic rings under photoredox conditions provide dearomatized 3-NHC-boryl-1,5-cycohexadienes, which are formally products of 1,4-hydroboration reactions. When regioisomers are possible, the more crowded (doubly ortho-substituted) product is formed preferably or exclusively. The mechanism may involve oxidation of the NHC-borane to an NHC-boryl radical, reduction of the electron-poor aromatic ring to a radical anion, coupling of the radical and the radical anion to give a cyclohexadienyl anion, and finally regioselective protonation. |
Author | Dai, Wen Curran, Dennis P Geib, Steven J |
AuthorAffiliation | Department of Chemistry |
AuthorAffiliation_xml | – name: Department of Chemistry |
Author_xml | – sequence: 1 givenname: Wen orcidid: 0000-0002-9098-5215 surname: Dai fullname: Dai, Wen – sequence: 2 givenname: Steven J orcidid: 0000-0002-9160-7857 surname: Geib fullname: Geib, Steven J – sequence: 3 givenname: Dennis P orcidid: 0000-0001-9644-7728 surname: Curran fullname: Curran, Dennis P email: curran@pitt.edu |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32101418$$D View this record in MEDLINE/PubMed |
BookMark | eNqNkctu1DAUhi3Uik4LO9YoSySa1vfEyzYqDFLVogrWkS_HKKOMXexEaHa8Aq_Ik-AwQ9mwYOVj-dOv3985RUchBkDoFcEXBFNyudE2X2CLMVf4GVoRQXEtCJVHaIUxpnXTSnaCTnPelCunLXmOThglmHDSrlBPznm93rkUTUx6GmKoHkDbZchV9NXNCHZKMdQfY0zVVYrbAtnqYQhfcmV21d3P7z_WMEGKdmfH8tLpZCBAdV3iAuQX6NjrMcPLw3mGPr-7-dSt69v79x-6q9taM4Wn2lDuDPeqoV4Cb1shnROSaCt8S5W3ToPxTWOZ4sQJZ40HwZxSlKuWKMfYGXqzz31M8esMeeq3Q7YwjqVEnHNPmZSSU8Gagp7vUZtizgl8_5iGrU67nuB-UdovSvuD0oK_PiTPZgvuCf7jsABv98A3MNFnO0Cw8IQV6YJKpliz6BeFbv-f7obp9066OIfp7x-Xeps4p1CM_rv0LywfopU |
CitedBy_id | crossref_primary_10_1002_ange_202314304 crossref_primary_10_1039_D4CC00398E crossref_primary_10_1002_advs_202307074 crossref_primary_10_1021_acs_orglett_2c03882 crossref_primary_10_1002_anie_202005749 crossref_primary_10_1002_tcr_202300172 crossref_primary_10_1039_D3QO01452E crossref_primary_10_1021_acs_orglett_1c02026 crossref_primary_10_1039_D2CS00344A crossref_primary_10_1021_acs_chemrev_0c01236 crossref_primary_10_1021_acs_orglett_3c04265 crossref_primary_10_1002_anie_202306846 crossref_primary_10_1016_j_ijhydene_2020_12_032 crossref_primary_10_1002_ange_202008358 crossref_primary_10_1002_anie_202402819 crossref_primary_10_1002_chem_202301199 crossref_primary_10_1021_acs_orglett_1c00230 crossref_primary_10_1038_s41467_024_48769_1 crossref_primary_10_1039_D3CS00889D crossref_primary_10_1039_D1CS00385B crossref_primary_10_1039_C9CS00311H crossref_primary_10_1039_D3QO00135K crossref_primary_10_1002_ange_202306846 crossref_primary_10_1021_acs_joc_3c01642 crossref_primary_10_1055_s_0042_1751512 crossref_primary_10_1039_D0CC06966C crossref_primary_10_1002_anie_202101874 crossref_primary_10_1002_chem_202101132 crossref_primary_10_1021_jacs_2c03673 crossref_primary_10_1039_D2OB00076H crossref_primary_10_1002_ange_202402819 crossref_primary_10_1021_acs_accounts_2c00752 crossref_primary_10_1002_anie_201915619 crossref_primary_10_1002_anie_202008358 crossref_primary_10_1016_j_cclet_2021_06_001 crossref_primary_10_1038_s41467_022_32238_8 crossref_primary_10_1039_D1RA08072E crossref_primary_10_1021_jacs_2c11664 crossref_primary_10_1002_ange_202005749 crossref_primary_10_1021_jacs_1c05852 crossref_primary_10_1002_ange_202101874 crossref_primary_10_1021_acscatal_4c00401 crossref_primary_10_1002_ange_201915619 crossref_primary_10_1021_acscatal_0c03808 crossref_primary_10_1039_D3SC01132A crossref_primary_10_1002_anie_202314304 crossref_primary_10_1007_s11426_023_1797_1 crossref_primary_10_6023_cjoc202103041 crossref_primary_10_1039_D4QO00058G crossref_primary_10_1021_acs_orglett_1c01270 crossref_primary_10_6023_cjoc202400011 crossref_primary_10_1038_s41586_021_03637_6 |
Cites_doi | 10.1021/acs.joc.6b01449 10.1021/jo202538x 10.1021/acs.chemrev.8b00561 10.1002/anie.201102717 10.1126/science.1213920 10.1021/ja904103x 10.1021/cr300503r 10.1016/j.tet.2006.04.096 10.1016/j.tet.2006.05.051 10.1039/b913880n 10.1002/anie.201913398 10.1021/acs.joc.5b01682 10.1002/anie.201800421 10.1021/ja909502q 10.1126/science.1239176 10.1002/anie.201903726 10.1002/anie.201911819 10.15227/orgsyn.092.0342 10.1016/j.tet.2003.12.015 10.1002/anie.201505090 10.1021/ol051027w 10.1021/ar2000698 10.1021/acs.chemrev.8b00079 10.2174/1385272819666150608220335 10.1021/jo00258a007 10.1002/0471264180.or042.01 10.1007/s11172-008-0116-6 10.1039/B913880N 10.1002/9781118754887.ch13 10.1016/B978-0-08-052349-1.00243-2 10.1002/9781118754887.ch15 10.1021/jo972197s 10.1002/0471264229.os092.26 10.1016/B978-0-08-052349-1.00108-6 |
ContentType | Journal Article |
DBID | 1KM AOWDO BLEPL DTL NPM AAYXX CITATION 7X8 |
DOI | 10.1021/jacs.0c00490 |
DatabaseName | Index Chemicus Web of Science - Science Citation Index Expanded - 2020 Web of Science Core Collection Science Citation Index Expanded PubMed CrossRef MEDLINE - Academic |
DatabaseTitle | Web of Science PubMed CrossRef MEDLINE - Academic |
DatabaseTitleList | Web of Science PubMed |
Database_xml | – sequence: 1 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: 2 dbid: 1KM name: Index Chemicus url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Enrichment Source Index Database |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Chemistry |
EISSN | 1520-5126 |
EndPage | 6267 |
ExternalDocumentID | 10_1021_jacs_0c00490 32101418 000526393700045 b163638712 |
Genre | Journal Article |
GrantInformation_xml | – fundername: U.S. National Science Foundation; National Science Foundation (NSF) grantid: CHE-1660927 |
GroupedDBID | - .K2 02 55A 5GY 5RE 5VS 7~N 85S AABXI ABFLS ABMVS ABPPZ ABPTK ABUCX ABUFD ACGFS ACJ ACNCT ACS AEESW AENEX AETEA AFEFF ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH BKOMP CS3 DU5 DZ EBS ED ED~ ET F5P GNL IH9 JG JG~ K2 LG6 P2P ROL RXW TAE TN5 UHB UI2 UKR UPT VF5 VG9 VQA W1F WH7 X XFK YZZ ZHY --- -DZ -ET -~X .DC 1KM 4.4 53G AAHBH ABJNI ABQRX ACBEA ACGFO ADHLV AGXLV AHGAQ BLEPL CUPRZ DTL GGK GROUPED_WOS_WEB_OF_SCIENCE IH2 XSW YQT ZCA ~02 NPM AAYXX CITATION 7X8 |
ID | FETCH-LOGICAL-a390t-b24db4f972f6e48856dd561ac5f829fcdaebf77c3941d5dcbfe53d99249819d33 |
IEDL.DBID | ACS |
ISICitedReferencesCount | 53 |
ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000526393700045 |
ISSN | 0002-7863 |
IngestDate | Sat Oct 05 06:15:58 EDT 2024 Thu Sep 26 18:20:51 EDT 2024 Sat Sep 28 08:28:40 EDT 2024 Tue Aug 27 15:41:34 EDT 2024 Fri Oct 18 20:12:18 EDT 2024 Thu Aug 27 22:10:37 EDT 2020 |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 13 |
Keywords | RADICAL DEAROMATIZATION GENERATION ARYLATION LIGHT ARENES PHOTOREDOX CATALYSIS |
Language | English |
LinkModel | DirectLink |
LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
MergedId | FETCHMERGED-LOGICAL-a390t-b24db4f972f6e48856dd561ac5f829fcdaebf77c3941d5dcbfe53d99249819d33 |
Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ORCID | 0000-0002-9160-7857 0000-0002-9098-5215 0000-0001-9644-7728 |
PMID | 32101418 |
PQID | 2366642537 |
PQPubID | 23479 |
PageCount | 7 |
ParticipantIDs | crossref_primary_10_1021_jacs_0c00490 webofscience_primary_000526393700045CitationCount pubmed_primary_32101418 acs_journals_10_1021_jacs_0c00490 proquest_miscellaneous_2366642537 webofscience_primary_000526393700045 |
ProviderPackageCode | JG~ 55A AABXI GNL VF5 7~N ACJ VG9 W1F ACS AEESW AFEFF .K2 ABMVS ABUCX IH9 BAANH AQSVZ ED~ UI2 |
PublicationCentury | 2000 |
PublicationDate | 2020-04-01 |
PublicationDateYYYYMMDD | 2020-04-01 |
PublicationDate_xml | – month: 04 year: 2020 text: 2020-04-01 day: 01 |
PublicationDecade | 2020 |
PublicationPlace | WASHINGTON |
PublicationPlace_xml | – name: WASHINGTON – name: United States |
PublicationTitle | Journal of the American Chemical Society |
PublicationTitleAbbrev | J AM CHEM SOC |
PublicationTitleAlternate | J. Am. Chem. Soc |
PublicationYear | 2020 |
Publisher | American Chemical Society Amer Chemical Soc |
Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc |
References | Prier, CK (WOS:000321810600018) 2013; 113 Curran, D. P. (000526393700045.7) 1991; 4 Xia, PJ (WOS:000508406200001) 2020; 59 Crich, D (WOS:000073266300061) 1998; 63 Xu, WG (WOS:000508742200001) 2020; 59 Studer, A (WOS:000368065300005) 2016; 55 Nesterov, V (WOS:000447354900006) 2018; 118 Smith, K (000526393700045.25) 1991; 8 Curran, DP (WOS:000297049300006) 2011; 50 Gardner, S (WOS:000211708000026) 2015; 92 McNally, A (WOS:000297313900045) 2011; 334 Vaganova, TA (WOS:000264400900006) 2008; 57 Pigge, F. C. (000526393700045.20) 2015 Crich, D (WOS:000188785600008) 2004; 60 Zhou, NN (WOS:000428350200021) 2018; 57 Walton, JC (WOS:000275085100051) 2010; 132 Heravi, MM (WOS:000357607200003) 2015; 19 HASEGAWA, E (WOS:A1988Q905200007) 1988; 53 Crich, D (WOS:000239218800025) 2006; 62 Rabideau, P. W. (000526393700045.22) 1992; 42 Zimmerman, HE (WOS:000301085600003) 2012; 45 Leifert, D (WOS:000526984800008) 2020; 59 Hayashi, T. (000526393700045.12) 1999; 1 Ueng, SH (WOS:000268806500080) 2009; 131 McFadden, T. (000526393700045.16) 2018 Shaw, MH (WOS:000381847600002) 2016; 81 Tucker, JW (WOS:000300340000001) 2012; 77 Narayanam, JMR (WOS:000285390900008) 2011; 40 Gardner, S (WOS:000362386400041) 2015; 80 Legare, MA (WOS:000477787600002) 2019; 119 Foubelo, F. (000526393700045.8) 2015 Crich, D (WOS:000231294400007) 2005; 7 Crich, D (WOS:000238674200012) 2006; 62 Schultz, DM (WOS:000332309600033) 2014; 343 Smith K. (ref5/cit5b) 1991; 8 ref15/cit15a Curran D. P. (ref16/cit16) 1991; 4 ref9/cit9b ref9/cit9a ref15/cit15b ref10/cit10a ref10/cit10b ref12/cit12c ref12/cit12b ref12/cit12a ref2/cit2c ref8/cit8 ref2/cit2b Foubelo F. (ref1/cit1) 2015 ref2/cit2a ref6/cit6d ref4/cit4a ref6/cit6e ref4/cit4b ref4/cit4c Hayashi T. (ref5/cit5a) 1999; 1 ref11/cit11b Pigge F. C. (ref3/cit3) 2015 ref11/cit11a ref13/cit13 ref7/cit7c ref7/cit7b ref7/cit7a ref4/cit4d ref4/cit4e ref6/cit6a ref6/cit6b ref6/cit6c |
References_xml | – volume: 42 start-page: 1 year: 1992 ident: 000526393700045.22 article-title: The Birch Reduction of Aromatic Compounds publication-title: Organic Reactions contributor: fullname: Rabideau, P. W. – volume: 19 start-page: 1491 year: 2015 ident: WOS:000357607200003 article-title: Recent Applications of Birch Reduction in Total Synthesis of Natural Products publication-title: CURRENT ORGANIC CHEMISTRY contributor: fullname: Heravi, MM – volume: 81 start-page: 6898 year: 2016 ident: WOS:000381847600002 article-title: Photoredox Catalysis in Organic Chemistry publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.6b01449 contributor: fullname: Shaw, MH – volume: 77 start-page: 1617 year: 2012 ident: WOS:000300340000001 article-title: Shining Light on Photoredox Catalysis: Theory and Synthetic Applications publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo202538x contributor: fullname: Tucker, JW – volume: 119 start-page: 8231 year: 2019 ident: WOS:000477787600002 article-title: Metallomimetic Chemistry of Boron publication-title: CHEMICAL REVIEWS doi: 10.1021/acs.chemrev.8b00561 contributor: fullname: Legare, MA – volume: 50 start-page: 10294 year: 2011 ident: WOS:000297049300006 article-title: Synthesis and Reactions of N-Heterocyclic Carbene Boranes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201102717 contributor: fullname: Curran, DP – volume: 1 start-page: 351 year: 1999 ident: 000526393700045.12 article-title: Hydroboration of Carbon-Carbon Double Bonds publication-title: Comprehensive Asymmetric Catalysis contributor: fullname: Hayashi, T. – start-page: 337 year: 2015 ident: 000526393700045.8 article-title: Reduction/hydrogenation of aromatic rings publication-title: Arene Chemistry: Reaction Mechanisms and Methods for Aromatic Compounds contributor: fullname: Foubelo, F. – volume: 334 start-page: 1114 year: 2011 ident: WOS:000297313900045 article-title: Discovery of an alpha-Amino C-H Arylation Reaction Using the Strategy of Accelerated Serendipity publication-title: SCIENCE doi: 10.1126/science.1213920 contributor: fullname: McNally, A – volume: 131 start-page: 11256 year: 2009 ident: WOS:000268806500080 article-title: N-Heterocyclic Carbene Boryl Radicals: A New Class of Boron-Centered Radical publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja904103x contributor: fullname: Ueng, SH – volume: 113 start-page: 5322 year: 2013 ident: WOS:000321810600018 article-title: Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis publication-title: CHEMICAL REVIEWS doi: 10.1021/cr300503r contributor: fullname: Prier, CK – volume: 4 start-page: 715 year: 1991 ident: 000526393700045.7 article-title: Radical Addition Reactions. publication-title: Compr. Org. Synth. contributor: fullname: Curran, D. P. – volume: 8 start-page: 703 year: 1991 ident: 000526393700045.25 article-title: Hydroboration of C=C and CC publication-title: Comprehensive Organic Synthesis contributor: fullname: Smith, K – start-page: 399 year: 2015 ident: 000526393700045.20 article-title: Dearomatization reactions: An overview publication-title: Arene Chemistry: Reaction Mechanisms and Methods for Aromatic Compounds contributor: fullname: Pigge, F. C. – volume: 57 start-page: 768 year: 2008 ident: WOS:000264400900006 article-title: Reductive activation of arenecarbonitriles for the reactions with some carbon-centered electrophiles: the reaction mechanisms and synthetic applications publication-title: RUSSIAN CHEMICAL BULLETIN contributor: fullname: Vaganova, TA – volume: 62 start-page: 6830 year: 2006 ident: WOS:000238674200012 article-title: Radical dearomatization of benzene leading to phenanthridine and phenanthridinone derivatives related to (+/-)-pancratistatin publication-title: TETRAHEDRON doi: 10.1016/j.tet.2006.04.096 contributor: fullname: Crich, D – volume: 62 start-page: 7824 year: 2006 ident: WOS:000239218800025 article-title: Radical dearomatization of arenes and heteroarenes publication-title: TETRAHEDRON doi: 10.1016/j.tet.2006.05.051 contributor: fullname: Crich, D – volume: 40 start-page: 102 year: 2011 ident: WOS:000285390900008 article-title: Visible light photoredox catalysis: applications in organic synthesis publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/b913880n contributor: fullname: Narayanam, JMR – volume: 59 start-page: 6706 year: 2020 ident: WOS:000508406200001 article-title: Photoinduced Single-Electron Transfer as an Enabling Principle in the Radical Borylation of Alkenes with NHC-Borane publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201913398 contributor: fullname: Xia, PJ – volume: 63 start-page: 2765 year: 1998 ident: WOS:000073266300061 article-title: Stannane-mediated radical addition to arenes. Generation of cyclohexadienyl radicals and increased propagation efficiency in the presence of catalytic benzeneselenol publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Crich, D – volume: 80 start-page: 9794 year: 2015 ident: WOS:000362386400041 article-title: Synthesis of 1,3-Dialkylimidazol-2-ylidene Boranes from 1,3-Dialkylimidazolium Iodides and Sodium Borohydride publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.5b01682 contributor: fullname: Gardner, S – start-page: 68 year: 2018 ident: 000526393700045.16 article-title: Synthesis and study of amidine-borane complexes publication-title: THESIS contributor: fullname: McFadden, T. – volume: 57 start-page: 3990 year: 2018 ident: WOS:000428350200021 article-title: Synergistic Photoredox Catalysis and Organocatalysis for Inverse Hydroboration of Imines publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201800421 contributor: fullname: Zhou, NN – volume: 53 start-page: 5435 year: 1988 ident: WOS:A1988Q905200007 article-title: PHOTOADDITIONS OF ETHERS, THIOETHERS, AND AMINES TO 9,10-DICYANOANTHRACENE BY ELECTRON-TRANSFER PATHWAYS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: HASEGAWA, E – volume: 132 start-page: 2350 year: 2010 ident: WOS:000275085100051 article-title: EPR Studies of the Generation, Structure, and Reactivity of N-Heterocyclic Carbene Borane Radicals publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja909502q contributor: fullname: Walton, JC – volume: 343 start-page: 985 year: 2014 ident: WOS:000332309600033 article-title: Solar Synthesis: Prospects in Visible Light Photocatalysis publication-title: SCIENCE doi: 10.1126/science.1239176 contributor: fullname: Schultz, DM – volume: 59 start-page: 74 year: 2020 ident: WOS:000526984800008 article-title: The Persistent Radical Effect in Organic Synthesis publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201903726 contributor: fullname: Leifert, D – volume: 59 start-page: 4009 year: 2020 ident: WOS:000508742200001 article-title: Visible-Light-Induced Selective Defluoroborylation of Polyfluoroarenes, gem-Difluoroalkenes, and Trifluoromethylalkenes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201911819 contributor: fullname: Xu, WG – volume: 92 start-page: 342 year: 2015 ident: WOS:000211708000026 article-title: 1,3-Dimethylimidazoyl-2-ylidene borane publication-title: ORGANIC SYNTHESES doi: 10.15227/orgsyn.092.0342 contributor: fullname: Gardner, S – volume: 60 start-page: 1513 year: 2004 ident: WOS:000188785600008 article-title: Synthesis of carbazomycin B by radical arylation of benzene publication-title: TETRAHEDRON doi: 10.1016/j.tet.2003.12.015 contributor: fullname: Crich, D – volume: 55 start-page: 58 year: 2016 ident: WOS:000368065300005 article-title: Catalysis of Radical Reactions: A Radical Chemistry Perspective publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201505090 contributor: fullname: Studer, A – volume: 7 start-page: 3625 year: 2005 ident: WOS:000231294400007 article-title: Facile dearomatizing radical arylation of furan and thiophene publication-title: ORGANIC LETTERS doi: 10.1021/ol051027w contributor: fullname: Crich, D – volume: 45 start-page: 164 year: 2012 ident: WOS:000301085600003 article-title: A Mechanistic Analysis of the Birch Reduction publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar2000698 contributor: fullname: Zimmerman, HE – volume: 118 start-page: 9678 year: 2018 ident: WOS:000447354900006 article-title: NHCs in Main Group Chemistry publication-title: CHEMICAL REVIEWS doi: 10.1021/acs.chemrev.8b00079 contributor: fullname: Nesterov, V – ident: ref2/cit2a doi: 10.2174/1385272819666150608220335 – ident: ref7/cit7b doi: 10.1021/jo00258a007 – ident: ref2/cit2c doi: 10.1002/0471264180.or042.01 – ident: ref7/cit7c doi: 10.1007/s11172-008-0116-6 – ident: ref9/cit9a doi: 10.1002/anie.201913398 – ident: ref12/cit12c doi: 10.1002/anie.201102717 – ident: ref15/cit15a doi: 10.1002/anie.201903726 – ident: ref6/cit6e doi: 10.1039/B913880N – ident: ref13/cit13 – ident: ref8/cit8 doi: 10.1002/anie.201800421 – ident: ref4/cit4c doi: 10.1016/j.tet.2006.04.096 – start-page: 337 volume-title: Arene Chemistry: Reaction Mechanisms and Methods for Aromatic Compounds, 1st Ed. year: 2015 ident: ref1/cit1 doi: 10.1002/9781118754887.ch13 contributor: fullname: Foubelo F. – volume: 1 start-page: 351 volume-title: Comprehensive Asymmetric Catalysis year: 1999 ident: ref5/cit5a contributor: fullname: Hayashi T. – ident: ref12/cit12a doi: 10.1021/acs.chemrev.8b00561 – ident: ref4/cit4b doi: 10.1016/j.tet.2006.05.051 – ident: ref2/cit2b doi: 10.1021/ar2000698 – ident: ref4/cit4e doi: 10.1016/j.tet.2003.12.015 – volume: 8 start-page: 703 volume-title: Comprehensive Organic Synthesis year: 1991 ident: ref5/cit5b doi: 10.1016/B978-0-08-052349-1.00243-2 contributor: fullname: Smith K. – ident: ref10/cit10b doi: 10.1021/ja904103x – ident: ref10/cit10a doi: 10.1021/ja909502q – start-page: 399 volume-title: Arene Chemistry: Reaction Mechanisms and Methods for Aromatic Compounds, 1st Ed. year: 2015 ident: ref3/cit3 doi: 10.1002/9781118754887.ch15 contributor: fullname: Pigge F. C. – ident: ref4/cit4a doi: 10.1021/jo972197s – ident: ref6/cit6c doi: 10.1126/science.1239176 – ident: ref11/cit11a doi: 10.1002/0471264229.os092.26 – ident: ref6/cit6d doi: 10.1021/jo202538x – ident: ref6/cit6a doi: 10.1021/acs.joc.6b01449 – ident: ref7/cit7a doi: 10.1126/science.1213920 – ident: ref4/cit4d doi: 10.1021/ol051027w – ident: ref6/cit6b doi: 10.1021/cr300503r – ident: ref9/cit9b doi: 10.1002/anie.201911819 – ident: ref11/cit11b doi: 10.1021/acs.joc.5b01682 – ident: ref12/cit12b doi: 10.1021/acs.chemrev.8b00079 – volume: 4 start-page: 715 volume-title: Comprehensive Organic Synthesis year: 1991 ident: ref16/cit16 doi: 10.1016/B978-0-08-052349-1.00108-6 contributor: fullname: Curran D. P. – ident: ref15/cit15b doi: 10.1002/anie.201505090 |
SSID | ssj0004281 |
Score | 2.57139 |
Snippet | Reactions of N-heterocyclic carbene boranes (NHC-boranes) with electron-poor aromatic rings under photoredox conditions provide dearomatized... |
Source | Web of Science |
SourceID | proquest crossref pubmed webofscience acs |
SourceType | Aggregation Database Index Database Enrichment Source Publisher |
StartPage | 6261 |
SubjectTerms | Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology |
Title | 1,4-Hydroboration Reactions of Electron-Poor Aromatic Rings by N‑Heterocyclic Carbene Boranes |
URI | http://dx.doi.org/10.1021/jacs.0c00490 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000526393700045 https://www.ncbi.nlm.nih.gov/pubmed/32101418 https://search.proquest.com/docview/2366642537 |
Volume | 142 |
WOS | 000526393700045 |
WOSCitedRecordID | wos000526393700045 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1LT9wwEB7R5UAvvB8pFBkJbniV2Hk4R4igq0pFiBaJWxS_Lq02aJM9LCf-Qv9if0nHebAUithr_JDsmXi-8cx8Bjgu0tigl8Gp1NKnoTURFZoZKlVog8ImKmiuBr5dxaPb8OtddDdPkH0ZwWeOH0hVQ181IaoPsMzQJDon6yz7Pq9_ZCLoYW4iYt4luL8c7QyQqv41QK9Q5X8NUGNsLtfgS1-y0-aY_BxOazlUD68ZHN9ZxzqsdniTnLUKsgFLZrwJK1n_zNsW5MFpSEczPSl7bSA3pq12qEhpyUX3Tg69LssJzlM2HK_kxt2wEzkjV38ef49cTk2pZuoXtmTFROIBSs5xOjxHt-H28uJHNqLdqwu04KlfU8lCLUObJsyiGIWIYq0RZBUqsoKlVunCSJskiqdhoCOtJMqX69T5cYguNOc7MBiXY7MHJGJGSZ9zVBODfqQoFBOxTDj3dYGoXntwhJuSd39NlTcBcYYOifvabZUHJ7248vuWgOONfke9LHPcQRf2wEWW0ypnHF00PJp44sFuK-SnmVwFUxAGwoPj51J_am_5cBxpYAN-PQgW6ZZ19OqOVqD-tMAi9-Ejc358kxF0AIN6MjWfEezU8rDR9L_M1Pg- |
link.rule.ids | 315,786,790,2782,27107,27955,27956,57091,57141 |
linkProvider | American Chemical Society |
linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1LT9wwEB5RONBLKaWP9EGNRG81Suw8nGMbgQKFFaIgcYvi16VogzbZw_bUv9C_yC_p2EmWlrbSXm1nZHsmnm9sz2eA_TpPDUYZnEotQxpbk1ChmaFSxTaqbaYivzVwNknLq_jkOrkektVdLgx2okVJrT_Ev2cXcDRBWBgqf1L1CDaSDB2dQ0LF1_s0SCaiEe1mIuXDPfeHXzs_pNo__dBf4PKffsj7nKMtmCx766-afDuYd_JAfX9A5LjycJ7CkwF9kk-9uWzDmpk-g81ifPRtB6roY0zLhZ41o22QC9PnPrSkseRweDWHnjfNDOU0nvGVXLj9diIXZHL342fpbtg0aqFusKaoZxKXU_IZxeGq-hyujg4vi5IObzDQmudhRyWLtYxtnjGLShUiSbVGyFWrxAqWW6VrI22WKZ7HkU60kqhtrnMX1SHW0Jy_gPVpMzWvgCTMKBlyjkZjMKoUtWIilRnnoa4R4-sA9nBSquEfait_PM4wPHGlw1QF8GHUWnXb03H8p93eqNIKZ9AdguAgm3lbMY4BGy5UPAvgZa_rpSSXzxTFkQhg_3flL-t7dhxHIeihcADRKs2KgWzdkQx0r1cY5HvYLC_PTqvT48mXN_CYuQjf3xV6C-vdbG7eIQzq5K43_l8kIgC4 |
linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1Lb9QwEB6VIgEX2vJMH9SVyg1XiZ2Hc2xDV8trVS1U6i2KXxfQptpkD8uJv8Bf7C_p2Em2UEAq19gZ2Z6xZ8Yz8xngsMpTg14Gp1LLkMbWJFRoZqhUsY0qm6nIXw18mqTj8_j9RXKxBtFQC4ODaJBS44P4bldfatsjDDioIGwIlY9W3YP7SRbFbi8eF59vSiGZiAaLNxMp73Pdb__tdJFqftdFfxiYf9VFXu-MNmC6GrFPN_l6tGjlkfp-C8zxv6a0CY97K5Qcd2KzBWtm9gQeFsPjb0-hjN7EdLzU83qQETI1XQ1EQ2pLTvvXc-hZXc-RTu2RX8nU3bsTuSSTqx8_xy7TplZL9Q1bimou8VglJ0gOT9dncD46_VKMaf8WA614HrZUsljL2OYZs8hcIZJUazS9KpVYwXKrdGWkzTLF8zjSiVYSuc517rw7tDk0589hfVbPzEsgCTNKhpyj8Bj0LkWlmEhlxnmoK7T1dQAHuChlv5ea0ofJGbop7mu_VAG8HjhXXnawHP_odzCwtcQVdMEQnGS9aErG0XHDA4tnAbzo-L2i5OqaULREAIe_CsCqvUPJcVCC3iQOILpLt6IHXXdgA-32HSa5Dw_O3o7Kj-8mH3bgEXOOvk8Z2oX1dr4we2gNtfKVl_9raa4DMg |
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=1%2C4-Hydroboration+Reactions+of+Electron-Poor+Aromatic+Rings+by+N-Heterocyclic+Carbene+Boranes&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.au=Dai%2C+Wen&rft.au=Geib%2C+Steven+J.&rft.au=Curran%2C+Dennis+P.&rft.date=2020-04-01&rft.pub=Amer+Chemical+Soc&rft.issn=0002-7863&rft.eissn=1520-5126&rft.volume=142&rft.issue=13&rft.spage=6261&rft.epage=6267&rft_id=info:doi/10.1021%2Fjacs.0c00490&rft_id=info%3Apmid%2F32101418&rft.externalDBID=n%2Fa&rft.externalDocID=000526393700045 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0002-7863&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0002-7863&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0002-7863&client=summon |