Synthesis of Benzylic Alcohols by C–H Oxidation
Selective methylene C–H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(methanesulfonyl) perox...
Saved in:
| Published in | Journal of the American Chemical Society Vol. 141; no. 45; pp. 17983 - 17988 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
13.11.2019
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | Selective methylene C–H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(methanesulfonyl) peroxide as an oxidant. We attempt to provide a rationale for the selectivity for monooxygenation, which is distinct from previous work; a proton-coupled electron transfer mechanism (PCET) may account for the difference in reactivity. We envision that our method will be useful for applications in the discovery of drugs and agrochemicals. |
|---|---|
| AbstractList | Selective methylene C-H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(methanesulfonyl) peroxide as an oxidant. We attempt to provide a rationale for the selectivity for monooxygenation, which is distinct from previous work; a proton-coupled electron transfer mechanism (PCET) may account for the difference in reactivity. We envision that our method will be useful for applications in the discovery of drugs and agrochemicals. Selective methylene C–H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(methanesulfonyl) peroxide as an oxidant. We attempt to provide a rationale for the selectivity for monooxygenation, which is distinct from previous work; a proton-coupled electron transfer mechanism (PCET) may account for the difference in reactivity. We envision that our method will be useful for applications in the discovery of drugs and agrochemicals. Selective methylene C–H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(methanesulfonyl) peroxide as an oxidant. We attempt to provide a rationale for the selectivity for monooxygenation, which is distinct from previous work; a proton-coupled electron transfer mechanism (PCET) may account for the difference in reactivity. We envision that our method will be useful for applications in the discovery of drugs and agrochemicals. |
| Author | Tanwar, Lalita Börgel, Jonas Ritter, Tobias |
| AuthorAffiliation | Max-Planck-Institut für Kohlenforschung |
| AuthorAffiliation_xml | – name: Max-Planck-Institut für Kohlenforschung |
| Author_xml | – sequence: 1 givenname: Lalita surname: Tanwar fullname: Tanwar, Lalita – sequence: 2 givenname: Jonas orcidid: 0000-0001-5301-8579 surname: Börgel fullname: Börgel, Jonas – sequence: 3 givenname: Tobias orcidid: 0000-0002-6957-450X surname: Ritter fullname: Ritter, Tobias email: ritter@mpi-muelheim.mpg.de |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31689095$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNkc1u1DAUhS1URKeFHWuUJRKk2E78t0FqI0qRKnUBrC3HuWY8ythtnLRMV32HvmGfpB5mGEDqgpVt-bv3nnvOAdoLMQBCrwk-IpiSDwtj05FqsaoVf4ZmhFFcMkL5HpphjGkpJK_20UFKi_ysqSQv0H5FuFRYsRkiX1dhnEPyqYiuOIFwu-q9LY57G-exT0W7KpqHu_uz4uKn78zoY3iJnjvTJ3i1PQ_R99NP35qz8vzi85fm-Lw0WcFYVqYSvOWOiY4QJyzDnAoiKqc6WhuHKRjWiVqClBKEAdWCxbbDpsWkBuuqQ_Rx0_dyapfQWQjjYHp9OfilGVY6Gq___Ql-rn_Ea83zwkyJ3ODttsEQryZIo176ZKHvTYA4JU0rQhkjitUZfb9B7RBTGsDtxhCs1y7rtct663LG3_wtbQf_tjUDcgPcQBtdsh6ChR22zkHJnATPN8wbP_4ytolTGHPpu_8v_bPjWt4iTkPIkTwt-hELD6ls |
| CitedBy_id | crossref_primary_10_1021_acs_orglett_0c03146 crossref_primary_10_1021_acs_orglett_0c03022 crossref_primary_10_1021_acs_orglett_1c01530 crossref_primary_10_1021_acscatal_2c01882 crossref_primary_10_1021_acs_joc_0c01720 crossref_primary_10_1016_j_tet_2021_132415 crossref_primary_10_1039_D4CC02501F crossref_primary_10_1021_jacs_3c00004 crossref_primary_10_1002_anie_202016679 crossref_primary_10_1039_D2CC02424A crossref_primary_10_1002_ange_202316444 crossref_primary_10_1002_chem_202003062 crossref_primary_10_1016_j_ces_2024_120056 crossref_primary_10_1021_acs_orglett_0c03108 crossref_primary_10_1016_j_apsb_2023_11_021 crossref_primary_10_1021_jacs_0c09106 crossref_primary_10_1021_jacs_2c13502 crossref_primary_10_1039_D0QO00785D crossref_primary_10_1039_D3GC02283H crossref_primary_10_1055_a_2076_9792 crossref_primary_10_1021_acs_orglett_3c04386 crossref_primary_10_1021_acs_chemrev_1c00795 crossref_primary_10_1021_acs_joc_3c02683 crossref_primary_10_1002_ange_202312808 crossref_primary_10_1021_acs_joc_2c00455 crossref_primary_10_1021_acs_jafc_1c01321 crossref_primary_10_1039_D2CY00164K crossref_primary_10_1016_j_chempr_2022_10_005 crossref_primary_10_1021_acs_orglett_9b04280 crossref_primary_10_1002_ange_202016679 crossref_primary_10_1002_cssc_202102326 crossref_primary_10_1021_acs_orglett_2c03777 crossref_primary_10_1016_S1872_2067_23_64615_7 crossref_primary_10_1039_D3SC00154G crossref_primary_10_1016_j_mcat_2022_112645 crossref_primary_10_1002_ange_202310138 crossref_primary_10_1021_acs_orglett_1c01645 crossref_primary_10_1002_cssc_202301754 crossref_primary_10_1021_acs_chemrev_1c00749 crossref_primary_10_1021_acs_joc_2c00440 crossref_primary_10_1021_acs_joc_2c02743 crossref_primary_10_1021_acs_accounts_3c00580 crossref_primary_10_1016_j_gresc_2023_01_005 crossref_primary_10_1016_j_jscs_2021_101397 crossref_primary_10_1038_s41467_022_31634_4 crossref_primary_10_1039_D3GC04209J crossref_primary_10_1021_acs_joc_2c02541 crossref_primary_10_1021_acssuschemeng_4c00063 crossref_primary_10_1002_anie_202310138 crossref_primary_10_1021_acs_orglett_3c02309 crossref_primary_10_1039_D4RA00775A crossref_primary_10_1002_ajoc_202300662 crossref_primary_10_1021_acs_orglett_2c03741 crossref_primary_10_1021_jacs_0c05362 crossref_primary_10_1021_acs_orglett_0c02238 crossref_primary_10_1021_acs_orglett_0c02239 crossref_primary_10_1039_D1CY00113B crossref_primary_10_1021_acs_orglett_1c00469 crossref_primary_10_3390_molecules28010223 crossref_primary_10_1002_slct_202204767 crossref_primary_10_1039_D3SC01752D crossref_primary_10_1002_ange_202406588 crossref_primary_10_1021_acs_joc_4c00708 crossref_primary_10_1039_C9SC06089H crossref_primary_10_1039_D4RA03791J crossref_primary_10_1016_j_tet_2020_131704 crossref_primary_10_1016_j_tetlet_2021_152950 crossref_primary_10_1016_j_isci_2022_104341 crossref_primary_10_1039_D3DT00851G crossref_primary_10_1038_s41570_022_00388_4 crossref_primary_10_1002_ejoc_202200051 crossref_primary_10_6023_cjoc202106001 crossref_primary_10_1021_acscatal_3c05428 crossref_primary_10_1021_jacs_3c01662 crossref_primary_10_1021_acs_joc_0c00803 crossref_primary_10_1038_s41467_021_22292_z crossref_primary_10_1021_jacs_1c13105 crossref_primary_10_1002_adsc_202301343 crossref_primary_10_1021_acssuschemeng_1c07026 crossref_primary_10_1002_anie_202316444 crossref_primary_10_1021_acssuschemeng_4c03719 crossref_primary_10_1002_chem_202302788 crossref_primary_10_1002_cssc_202301138 crossref_primary_10_1021_jacs_3c14366 crossref_primary_10_1002_cssc_202301015 crossref_primary_10_1039_D4OB00268G crossref_primary_10_1002_anie_202406588 crossref_primary_10_1002_chem_202101232 crossref_primary_10_1021_acscatal_0c02321 crossref_primary_10_1055_s_0042_1751537 crossref_primary_10_1055_a_2017_6065 crossref_primary_10_1021_acs_joc_2c02363 crossref_primary_10_1002_anie_202312808 |
| Cites_doi | 10.1126/science.1148597 10.1021/ja505136j 10.1038/s41557-018-0175-8 10.1039/c9sc02609f 10.1021/jacs.5b04087 10.1021/jacs.8b05195 10.1039/c2sc20115a 10.1039/c2ee03361e 10.1126/science.1183602 10.1021/cs300001x 10.1021/jacs.7b09744 10.1021/jacs.8b09208 10.1021/acs.inorgchem.9b01326 10.1002/anie.201910602 10.1021/ja012732c 10.1039/c5cs00628g 10.1021/jacs.5b10299 10.1039/c8cc08768g 10.1021/ja004218x 10.1055/s-0034-1379304 10.1007/s41061-016-0030-6 10.1016/j.tetlet.2011.06.118 10.1039/c5cc07647a 10.1002/anie.201712340 10.1021/acs.orglett.9b01607 10.1021/cr100085k 10.1021/ol300853z 10.1016/j.bbabio.2003.07.002 10.1039/c7sc02773g 10.1021/acs.accounts.6b00272 10.1021/ja8031218 10.1002/anie.201602644 10.1021/ja407388y 10.1021/ja9642572 10.1007/978-3-319-12108-6_4 10.1039/C7SC02773G 10.1039/C9SC02609F 10.26434/chemrxiv.8159645.v1 10.1002/hlca.200690208 10.1016/S0040-4039(01)93893-6 10.1039/C5CC07647A 10.1039/C5CS00628G 10.1021/jo00298a046 10.1021/ja01053a043 10.1139/v66-359 10.1002/med.1017 10.1139/v89-182 10.1039/C8CC08768G 10.1016/S0040-4020(98)00603-6 10.1021/ja00424a043 10.1021/ja00204a047 10.1016/0040-4020(79)87003-9 10.1021/cr00002a004 |
| ContentType | Journal Article |
| Copyright | Copyright © 2019 American Chemical Society 2019 American Chemical Society |
| Copyright_xml | – notice: Copyright © 2019 American Chemical Society 2019 American Chemical Society |
| DBID | 1KM 1KN AAWJD BLEPL DTL NPM AAYXX CITATION 7X8 5PM |
| DOI | 10.1021/jacs.9b09496 |
| DatabaseName | Index Chemicus Current Chemical Reactions Web of Science - Science Citation Index Expanded - 2019 Web of Science Core Collection Science Citation Index Expanded PubMed CrossRef MEDLINE - Academic PubMed Central (Full Participant titles) |
| 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: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1520-5126 |
| EndPage | 17988 |
| ExternalDocumentID | 10_1021_jacs_9b09496 31689095 000498281600006 c820363146 |
| Genre | Journal Article |
| GrantInformation_xml | – fundername: Fond der Chemischen Industrie; Fonds der Chemischen Industrie – fundername: MPI fur Kohlenforschung |
| GroupedDBID | - .K2 02 53G 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 1KN 4.4 AAHBH ABJNI ABQRX ACBEA ACGFO ADHLV AGXLV AHGAQ BLEPL CUPRZ DTL GGK GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED IH2 XSW YQT ZCA ~02 NPM AAYXX CITATION 7X8 5PM |
| ID | FETCH-LOGICAL-a520t-3a376b6f57d11f7c50627173f9d24af02ea5d748e888e7ae9bec0cd0ab014ecf3 |
| IEDL.DBID | ACS |
| ISICitedReferencesCount | 92 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000498281600006 |
| ISSN | 0002-7863 |
| IngestDate | Tue Sep 17 21:24:43 EDT 2024 Sat Oct 05 04:58:24 EDT 2024 Thu Sep 26 18:20:48 EDT 2024 Sat Sep 28 08:30:38 EDT 2024 Wed Sep 18 05:42:13 EDT 2024 Fri Oct 25 20:05:36 EDT 2024 Thu Aug 27 13:44:03 EDT 2020 |
| IsDoiOpenAccess | true |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 45 |
| Keywords | FUNCTIONALIZATION COMPLEX HYDROGEN-ATOM ABSTRACTION COUPLED ELECTRON-TRANSFER ASYMMETRIC HYDROXYLATION OXYGENATION BONDS RADICALS EFFICIENT HYDROXYPHTHALIMIDE |
| Language | English |
| License | This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-a520t-3a376b6f57d11f7c50627173f9d24af02ea5d748e888e7ae9bec0cd0ab014ecf3 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0002-6957-450X 0000-0001-5301-8579 |
| OpenAccessLink | https://pubmed.ncbi.nlm.nih.gov/PMC6863597 |
| PMID | 31689095 |
| PQID | 2312551954 |
| PQPubID | 23479 |
| PageCount | 6 |
| ParticipantIDs | proquest_miscellaneous_2312551954 pubmed_primary_31689095 crossref_primary_10_1021_jacs_9b09496 pubmedcentral_primary_oai_pubmedcentral_nih_gov_6863597 webofscience_primary_000498281600006 webofscience_primary_000498281600006CitationCount acs_journals_10_1021_jacs_9b09496 |
| 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 | 2019-11-13 |
| PublicationDateYYYYMMDD | 2019-11-13 |
| PublicationDate_xml | – month: 11 year: 2019 text: 2019-11-13 day: 13 |
| PublicationDecade | 2010 |
| 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 | 2019 |
| Publisher | American Chemical Society Amer Chemical Soc |
| Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc |
| References | Mayer, JM (WOS:000221079300006) 2004; 1655 KENNEDY, BR (WOS:A19668418800003) 1966; 44 LEWIS, ES (WOS:A1976BN52500043) 1976; 98 Marko, JA (WOS:000457296200008) 2019; 55 Li, CS (WOS:000304365000024) 2012; 3 Burg, F (WOS:000426490700035) 2018; 57 Fasan, R (WOS:000302387600022) 2012; 2 Rafiee, M (WOS:000422813300006) 2018; 140 Hamada, T (WOS:000075190800007) 1998; 54 Yayla, HG (WOS:000345902500001) 2014; 25 Ryan, MC (WOS:000480371400075) 2019; 58 Gormisky, PE (WOS:000330162900014) 2013; 135 Moriyama, K (WOS:000303492200057) 2012; 14 GROVES, JT (WOS:A1989AX04300047) 1989; 111 TOTHEROW, WD (WOS:A1969E745500043) 1969; 91 Genovino, J (WOS:000387028000003) 2016; 55 KIM, YH (WOS:A1989CB56400028) 1989; 30 GROVES, JT (WOS:A1990DF28600046) 1990; 55 Thompson, TN (WOS:000170474700005) 2001; 21 Das, A (WOS:000481422800003) 2019; 10 Gentry, EC (WOS:000381654700011) 2016; 49 Sakamoto, R (WOS:000371477100003) 2016; 52 Nicolaou, KC (WOS:000167806300047) 2001; 123 Chen, MS (WOS:000250583900037) 2007; 318 WARD, DE (WOS:A1989AF89300014) 1989; 67 White, MC (WOS:000449239700001) 2018; 140 Zhang, GY (WOS:000474795200020) 2019; 21 Li, GX (WOS:000411730500058) 2017; 8 HANSCH, C (WOS:A1991FE92400004) 1991; 91 Lee, JM (WOS:000256962000025) 2008; 130 BROWN, HC (WOS:A1979GP78500003) 1979; 35 Borgel, J (WOS:000451933100008) 2018; 140 Howell, JM (WOS:000366004700010) 2015; 137 Hu, H (000498281600006.22) 2019 Mayer, JM (WOS:000178019700048) 2002; 124 Arafat, AM (WOS:000241928300012) 2006; 89 Zhao, JP (WOS:000459340400008) 2019; 11 Kamijo, S (WOS:000294145600017) 2011; 52 Miller, DC (WOS:000386346600009) 2016; 374 Pitts, CR (WOS:000338980500036) 2014; 136 Chen, MS (WOS:000274020500034) 2010; 327 Kim, C (WOS:A1997XG88200027) 1997; 119 Hammes-Schiffer, S (WOS:000358556200001) 2015; 137 Warren, JJ (WOS:000285275700003) 2010; 110 Ortiz de Montellano, P. R (000498281600006.10) 2015 Beale, J. M (000498281600006.2) 2011 Lee, BJ (WOS:000496874000001) 2020; 59 Hammes-Schiffer, S (WOS:000305530900002) 2012; 5 Cernak, T (WOS:000369532200007) 2016; 45 ref9/cit9 ref3/cit3 Beale J. M. (ref2/cit2) 2011 ref13/cit13a ref16/cit16 ref13/cit13b ref27/cit27a ref13/cit13c ref13/cit13d ref27/cit27b ref23/cit23 ref20/cit20 ref5/cit5b ref17/cit17 ref5/cit5c ref10/cit10 ref5/cit5a ref22/cit22a ref11/cit11b ref11/cit11a ref22/cit22c ref22/cit22b ref19/cit19a ref15/cit15a ref19/cit19b ref15/cit15b ref25/cit25 ref15/cit15c ref8/cit8a ref8/cit8b ref21/cit21b ref21/cit21c ref14/cit14 ref21/cit21a Ortiz de Montellano P. R. (ref1/cit1) 2015 ref26/cit26 ref18/cit18b ref4/cit4a ref4/cit4b ref18/cit18a ref24/cit24c ref24/cit24b ref12/cit12 ref24/cit24e ref24/cit24d ref24/cit24a ref6/cit6a ref6/cit6b ref7/cit7 |
| References_xml | – volume: 111 start-page: 8537 year: 1989 ident: WOS:A1989AX04300047 article-title: ASYMMETRIC HYDROXYLATION BY A CHIRAL IRON PORPHYRIN publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: GROVES, JT – volume: 318 start-page: 783 year: 2007 ident: WOS:000250583900037 article-title: A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis publication-title: SCIENCE doi: 10.1126/science.1148597 contributor: fullname: Chen, MS – volume: 136 start-page: 9780 year: 2014 ident: WOS:000338980500036 article-title: Direct, Catalytic Monofluorination of sp(3) C-H Bonds: A Radical-Based Mechanism with Ionic Selectivity publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja505136j contributor: fullname: Pitts, CR – volume: 11 start-page: 213 year: 2019 ident: WOS:000459340400008 article-title: Chemoselective methylene oxidation in aromatic molecules publication-title: NATURE CHEMISTRY doi: 10.1038/s41557-018-0175-8 contributor: fullname: Zhao, JP – volume: 10 start-page: 7542 year: 2019 ident: WOS:000481422800003 article-title: Electrochemical C-H oxygenation and alcohol dehydrogenation involving Fe-oxo species using water as the oxygen source publication-title: CHEMICAL SCIENCE doi: 10.1039/c9sc02609f contributor: fullname: Das, A – volume: 137 start-page: 8860 year: 2015 ident: WOS:000358556200001 article-title: Proton-Coupled Electron Transfer: Moving Together and Charging Forward publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.5b04087 contributor: fullname: Hammes-Schiffer, S – volume: 140 start-page: 13988 year: 2018 ident: WOS:000449239700001 article-title: Aliphatic C-H Oxidations for Late-Stage Functionalization publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.8b05195 contributor: fullname: White, MC – volume: 3 start-page: 1903 year: 2012 ident: WOS:000304365000024 article-title: Blended hydrogen atom abstraction and proton-coupled electron transfer mechanisms of closed-shell molecules publication-title: CHEMICAL SCIENCE doi: 10.1039/c2sc20115a contributor: fullname: Li, CS – volume: 5 start-page: 7696 year: 2012 ident: WOS:000305530900002 article-title: Proton-coupled electron transfer: classification scheme and guide to theoretical methods publication-title: ENERGY & ENVIRONMENTAL SCIENCE doi: 10.1039/c2ee03361e contributor: fullname: Hammes-Schiffer, S – volume: 91 start-page: 165 year: 1991 ident: WOS:A1991FE92400004 article-title: A SURVEY OF HAMMETT SUBSTITUENT CONSTANTS AND RESONANCE AND FIELD PARAMETERS publication-title: CHEMICAL REVIEWS contributor: fullname: HANSCH, C – volume: 327 start-page: 566 year: 2010 ident: WOS:000274020500034 article-title: Combined Effects on Selectivity in Fe-Catalyzed Methylene Oxidation publication-title: SCIENCE doi: 10.1126/science.1183602 contributor: fullname: Chen, MS – year: 2019 ident: 000498281600006.22 article-title: Copper-Catalyzed Benzylic C H Coupling with Alcohols via Radical Relay publication-title: COPPER CATALYZED BEN contributor: fullname: Hu, H – volume: 2 start-page: 647 year: 2012 ident: WOS:000302387600022 article-title: Tuning P450 Enzymes as Oxidation Catalysts publication-title: ACS CATALYSIS doi: 10.1021/cs300001x contributor: fullname: Fasan, R – volume: 35 start-page: 567 year: 1979 ident: WOS:A1979GP78500003 article-title: 40 YEARS OF HYDRIDE REDUCTIONS publication-title: TETRAHEDRON contributor: fullname: BROWN, HC – volume: 140 start-page: 22 year: 2018 ident: WOS:000422813300006 article-title: &ITN&IT-Hydroxyphthalimide-Mediated Electrochemical Iodination of Methylarenes and Comparison to Electron-Transfer-Initiated C-H Functionalization publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b09744 contributor: fullname: Rafiee, M – volume: 91 start-page: 7150 year: 1969 ident: WOS:A1969E745500043 article-title: STERIC EFFECTS IN HYDROGEN ATOM ABSTRACTIONS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: TOTHEROW, WD – volume: 140 start-page: 16026 year: 2018 ident: WOS:000451933100008 article-title: Late-Stage Aromatic C-H Oxygenation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.8b09208 contributor: fullname: Borgel, J – volume: 58 start-page: 10194 year: 2019 ident: WOS:000480371400075 article-title: Copper/TEMPO Redox Redux: Analysis of PCET Oxidation of TEMPOH by Copper(II) and the Reaction of TEMPO with Copper(I) publication-title: INORGANIC CHEMISTRY doi: 10.1021/acs.inorgchem.9b01326 contributor: fullname: Ryan, MC – volume: 89 start-page: 2226 year: 2006 ident: WOS:000241928300012 article-title: Reactions of alkyl radicals with substituted toluenes and the effect of substituents on dissociation energies of benzyl C-H bonds publication-title: HELVETICA CHIMICA ACTA contributor: fullname: Arafat, AM – volume: 59 start-page: 197 year: 2020 ident: WOS:000496874000001 article-title: Site-Selective Alkoxylation of Benzylic C-H Bonds by Photoredox Catalysis publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201910602 contributor: fullname: Lee, BJ – volume: 124 start-page: 11142 year: 2002 ident: WOS:000178019700048 article-title: Proton-coupled electron transfer versus hydrogen atom transfer in benzyl/toluene, methoxyl/methanol, and phenoxyl/phenol self-exchange reactions publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja012732c contributor: fullname: Mayer, JM – volume: 45 start-page: 546 year: 2016 ident: WOS:000369532200007 article-title: The medicinal chemist's toolbox for late stage functionalization of drug-like molecules publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c5cs00628g contributor: fullname: Cernak, T – volume: 21 start-page: 412 year: 2001 ident: WOS:000170474700005 article-title: Optimization of metabolic stability as a goal of modern drug design publication-title: MEDICINAL RESEARCH REVIEWS contributor: fullname: Thompson, TN – year: 2011 ident: 000498281600006.2 publication-title: Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry contributor: fullname: Beale, J. M – volume: 137 start-page: 14590 year: 2015 ident: WOS:000366004700010 article-title: Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.5b10299 contributor: fullname: Howell, JM – volume: 55 start-page: 937 year: 2019 ident: WOS:000457296200008 article-title: Electrochemical benzylic oxidation of C-H bonds publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c8cc08768g contributor: fullname: Marko, JA – start-page: 111 year: 2015 ident: 000498281600006.10 article-title: Substrate Oxidation by Cytochrome P450 Enzymes publication-title: Cytochrome P450: Structure, Mechanism, and Biochemistry contributor: fullname: Ortiz de Montellano, P. R – volume: 123 start-page: 3183 year: 2001 ident: WOS:000167806300047 article-title: Selective oxidation at carbon adjacent to aromatic systems with IBX publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja004218x contributor: fullname: Nicolaou, KC – volume: 67 start-page: 1206 year: 1989 ident: WOS:A1989AF89300014 article-title: CHEMOSELECTIVE REDUCTIONS WITH SODIUM-BOROHYDRIDE publication-title: CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE contributor: fullname: WARD, DE – volume: 98 start-page: 2264 year: 1976 ident: WOS:A1976BN52500043 article-title: ISOTOPE-EFFECTS IN HYDROGEN-ATOM TRANSFER .7. BENZYLIC HYDROGEN ABSTRACTION BY TERT-BUTOXY AND OTHER RADICALS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: LEWIS, ES – volume: 25 start-page: 2819 year: 2014 ident: WOS:000345902500001 article-title: Proton-Coupled Electron Transfer in Organic Synthesis: Novel Homolytic Bond Activations and Catalytic Asymmetric Reactions with Free Radicals publication-title: SYNLETT doi: 10.1055/s-0034-1379304 contributor: fullname: Yayla, HG – volume: 44 start-page: 2381 year: 1966 ident: WOS:A19668418800003 article-title: REACTIONS OF ALKOXY RADICALS .I. HYDROGEN ATOM ABSTRACTION FROM SUBSTITUTED TOLUENES publication-title: CANADIAN JOURNAL OF CHEMISTRY contributor: fullname: KENNEDY, BR – volume: 54 start-page: 10017 year: 1998 ident: WOS:000075190800007 article-title: Highly enantioselective benzylic hydroxylation with concave type of (salen)manganese(III) complex publication-title: TETRAHEDRON contributor: fullname: Hamada, T – volume: 374 start-page: ARTN 30 year: 2016 ident: WOS:000386346600009 article-title: Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities publication-title: TOPICS IN CURRENT CHEMISTRY doi: 10.1007/s41061-016-0030-6 contributor: fullname: Miller, DC – volume: 52 start-page: 4654 year: 2011 ident: WOS:000294145600017 article-title: Direct oxidative installation of nitrooxy group at benzylic positions and its transformation into various functionalities publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2011.06.118 contributor: fullname: Kamijo, S – volume: 52 start-page: 3758 year: 2016 ident: WOS:000371477100003 article-title: Efficient photolytic C-H bond functionalization of alkylbenzene with hypervalent iodine(III) reagent publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c5cc07647a contributor: fullname: Sakamoto, R – volume: 57 start-page: 2953 year: 2018 ident: WOS:000426490700035 article-title: Site- and Enantioselective C-H Oxygenation Catalyzed by a Chiral Manganese Porphyrin Complex with a Remote Binding Site publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201712340 contributor: fullname: Burg, F – volume: 21 start-page: 5015 year: 2019 ident: WOS:000474795200020 article-title: Proton-Coupled Electron Transfer Enables Tandem Radical Relay for Asymmetric Copper-Catalyzed Phosphinoylcyanation of Styrenes publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.9b01607 contributor: fullname: Zhang, GY – volume: 110 start-page: 6961 year: 2010 ident: WOS:000285275700003 article-title: Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications publication-title: CHEMICAL REVIEWS doi: 10.1021/cr100085k contributor: fullname: Warren, JJ – volume: 14 start-page: 2414 year: 2012 ident: WOS:000303492200057 article-title: Direct and Selective Benzylic Oxidation of Alkylarenes via C-H Abstraction Using Alkali Metal Bromides publication-title: ORGANIC LETTERS doi: 10.1021/ol300853z contributor: fullname: Moriyama, K – volume: 1655 start-page: 51 year: 2004 ident: WOS:000221079300006 article-title: Thermodynamics and kinetics of proton-coupled electron transfer: stepwise vs. concerted pathways publication-title: BIOCHIMICA ET BIOPHYSICA ACTA-BIOENERGETICS doi: 10.1016/j.bbabio.2003.07.002 contributor: fullname: Mayer, JM – volume: 8 start-page: 7180 year: 2017 ident: WOS:000411730500058 article-title: A unified photoredox-catalysis strategy for C(sp(3))-H hydroxylation and amidation using hypervalent iodine publication-title: CHEMICAL SCIENCE doi: 10.1039/c7sc02773g contributor: fullname: Li, GX – volume: 119 start-page: 5964 year: 1997 ident: WOS:A1997XG88200027 article-title: Stereospecific alkane hydroxylation with H2O2 catalyzed by an iron(II)-tris(2-pyridylmethyl)amine complex publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Kim, C – volume: 49 start-page: 1546 year: 2016 ident: WOS:000381654700011 article-title: Synthetic Applications of Proton-Coupled Electron Transfer publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/acs.accounts.6b00272 contributor: fullname: Gentry, EC – volume: 130 start-page: 7824 year: 2008 ident: WOS:000256962000025 article-title: Cu-facilitated C-O bond formation using N-hydroxyphthalimide: Efficient and selective functionalization of benzyl and allylic C-H bonds publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja8031218 contributor: fullname: Lee, JM – volume: 55 start-page: 14217 year: 2016 ident: WOS:000387028000003 article-title: Accessing Drug Metabolites via Transition-Metal Catalyzed C-H Oxidation: The Liver as Synthetic Inspiration publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201602644 contributor: fullname: Genovino, J – volume: 135 start-page: 14052 year: 2013 ident: WOS:000330162900014 article-title: Catalyst-Controlled Aliphatic C-H Oxidations with a Predictive Model for Site-Selectivity publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja407388y contributor: fullname: Gormisky, PE – volume: 30 start-page: 6357 year: 1989 ident: WOS:A1989CB56400028 article-title: OXIDATION OF BENZYLIC METHYLENE-COMPOUNDS TO KETONES WITH 2-NITROBENZENE PEROXYSULFONYL RADICAL FORMED FROM ITS CHLORIDE AND SUPEROXIDE publication-title: TETRAHEDRON LETTERS contributor: fullname: KIM, YH – volume: 55 start-page: 3628 year: 1990 ident: WOS:A1990DF28600046 article-title: ASYMMETRIC HYDROXYLATION, EPOXIDATION, AND SULFOXIDATION CATALYZED BY VAULTED BINAPHTHYL METALLOPORPHYRINS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: GROVES, JT – ident: ref11/cit11b doi: 10.1021/ja9642572 – ident: ref14/cit14 doi: 10.1002/anie.201712340 – start-page: 111 volume-title: Cytochrome P450: Structure, Mechanism, and Biochemistry year: 2015 ident: ref1/cit1 doi: 10.1007/978-3-319-12108-6_4 contributor: fullname: Ortiz de Montellano P. R. – ident: ref18/cit18b doi: 10.1039/C7SC02773G – ident: ref20/cit20 doi: 10.1021/jacs.8b09208 – ident: ref24/cit24b doi: 10.1021/jacs.5b04087 – ident: ref21/cit21c doi: 10.1021/ja505136j – volume-title: Wilson and Gisvold’s Textbook of Organic Medicinal and Pharmaceutical Chemistry year: 2011 ident: ref2/cit2 contributor: fullname: Beale J. M. – ident: ref16/cit16 doi: 10.1021/ja8031218 – ident: ref5/cit5a doi: 10.1021/jacs.8b05195 – ident: ref5/cit5b doi: 10.1039/C9SC02609F – ident: ref24/cit24c doi: 10.1007/s41061-016-0030-6 – ident: ref19/cit19a doi: 10.26434/chemrxiv.8159645.v1 – ident: ref15/cit15c doi: 10.1021/ja004218x – ident: ref24/cit24e doi: 10.1016/j.bbabio.2003.07.002 – ident: ref27/cit27a doi: 10.1002/hlca.200690208 – ident: ref15/cit15b doi: 10.1016/S0040-4039(01)93893-6 – ident: ref18/cit18a doi: 10.1039/C5CC07647A – ident: ref4/cit4b doi: 10.1039/C5CS00628G – ident: ref13/cit13c doi: 10.1021/jacs.5b10299 – ident: ref7/cit7 doi: 10.1021/jo00298a046 – ident: ref23/cit23 doi: 10.1021/ja01053a043 – ident: ref15/cit15a doi: 10.1021/ol300853z – ident: ref21/cit21a doi: 10.1021/acs.inorgchem.9b01326 – ident: ref8/cit8a doi: 10.1139/v66-359 – ident: ref22/cit22b doi: 10.1021/cr100085k – ident: ref27/cit27b doi: 10.1021/jacs.7b09744 – ident: ref9/cit9 doi: 10.1021/cs300001x – ident: ref3/cit3 doi: 10.1002/med.1017 – ident: ref13/cit13a doi: 10.1126/science.1183602 – ident: ref6/cit6b doi: 10.1139/v89-182 – ident: ref5/cit5c doi: 10.1039/C8CC08768G – ident: ref13/cit13b doi: 10.1021/ja407388y – ident: ref22/cit22c doi: 10.1055/s-0034-1379304 – ident: ref24/cit24a doi: 10.1039/c2ee03361e – ident: ref4/cit4a doi: 10.1002/anie.201602644 – ident: ref11/cit11a doi: 10.1016/S0040-4020(98)00603-6 – ident: ref8/cit8b doi: 10.1021/ja00424a043 – ident: ref10/cit10 doi: 10.1021/ja00204a047 – ident: ref17/cit17 doi: 10.1016/j.tetlet.2011.06.118 – ident: ref6/cit6a doi: 10.1016/0040-4020(79)87003-9 – ident: ref19/cit19b doi: 10.1002/anie.201910602 – ident: ref26/cit26 doi: 10.1021/cr00002a004 – ident: ref21/cit21b doi: 10.1021/acs.orglett.9b01607 – ident: ref13/cit13d doi: 10.1038/s41557-018-0175-8 – ident: ref25/cit25 doi: 10.1039/c2sc20115a – ident: ref24/cit24d doi: 10.1021/acs.accounts.6b00272 – ident: ref12/cit12 doi: 10.1126/science.1148597 – ident: ref22/cit22a doi: 10.1021/ja012732c |
| SSID | ssj0004281 |
| Score | 2.6215432 |
| Snippet | Selective methylene C–H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for... Selective methylene C-H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for... Selective methylene C–H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for... |
| Source | Web of Science |
| SourceID | pubmedcentral proquest crossref pubmed webofscience acs |
| SourceType | Open Access Repository Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 17983 |
| SubjectTerms | Chemistry Chemistry, Multidisciplinary Communication Physical Sciences Science & Technology |
| Title | Synthesis of Benzylic Alcohols by C–H Oxidation |
| URI | http://dx.doi.org/10.1021/jacs.9b09496 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000498281600006 https://www.ncbi.nlm.nih.gov/pubmed/31689095 https://search.proquest.com/docview/2312551954 https://pubmed.ncbi.nlm.nih.gov/PMC6863597 |
| Volume | 141 |
| WOS | 000498281600006 |
| WOSCitedRecordID | wos000498281600006 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Lb9QwEB5BOcCF8iaFolQqx6wc20ns4zaiXXGAQ6nUW-SnWIGyiGQltif-Q_9hf0nHeWzZLYheEzvSeOzM92nG3wAcSu8U0cInmlGfcG5ponNBEsMs11TyADpCtcWnfHbGP55n5zcFstsZfBr0gUwzkRppiMzvwwNaEBlKt6bl6c39RyrSEeYWImdDgfv27BCATLMZgG6hyr8XR24FpC74HO_CyXiFp685-TZZtnpiLm4rOv7HrifweMCf8bTfME_hnqufwcNybPv2HNLTVY2gsJk38cLHR66-WH2fm3jat9JtYr2Ky6vfl7P4869534_pBZwdf_hSzpKhr0KiMkrahCn8q-jcZ4VNU1-YLEgVpwXz0lKuPKFOZbbgwiE7doVyEv1MjCVKI59yxrOXsFMvavcaYsGl0EQJbTTyOGJlzoVV1ArKmTdMRXCAZlbDuWiqLuVNkXKEp4PxEbwfHVL96CU2_jHuYPRWhWsSEhuqdotlUyFGRWYUtOsieNV7b_2l0JhLIo6MoNjw63pA0NfefFPPv3Y62zluJeRbERz-uQPWEzt2hYQ1zbugH0F6l2HlIL0eJAfavTsszxt4hCBNhvuPKXsLO-3PpdtHINTqd90puAaXbwJ4 |
| link.rule.ids | 230,315,786,790,891,2778,27098,27946,27947,57082,57132 |
| linkProvider | American Chemical Society |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1NT9wwEB1RONALhX7QlJYGiR6DEttJ7CONQAul2wMgcYv8qa6KshXJSl1O_Q_9h_0ljJPs0t220l4d27I9duY9efwG4FA4K2PFXaQocRFjhkQq43GkqWGKCOZBh4-2GGaDa3Z-k970j9X9WxgcRI091e0l_qO6gJcJwkKhkI2I7AlspDn6Lo-EisvHZ5CEJzO0m_OM9nHuy629H9L1oh_6C1z-O0ZyyS-1Puj0GQzno29DT74dTRp1pO-XhB1Xnt42bPVoNDzuts8OrNnqOWwWsyRwLyC5nFYIEetRHY5d-NFW99PbkQ6Pu8S6daimYfH7569B-OXHqMvO9BKuT0-uikHUZ1mIZEriJqIS_zEqc2luksTlOvXCxUlOnTCESRcTK1OTM26RK9tcWoFWj7WJpUJ2ZbWjr2C9Glf2NYScCa5iyZVWyOpiIzLGjSSGE0adpjKAA5xm2Z-SumwvwAkSEF_aTz6ADzO7lN87wY3_1DuYGa3ENfHXHLKy40ldImJFnuSV7ALY7Yw478mn6RKIKgPIF8w7r-DVthe_VKOvrep2hjsK2VcAh39uhHnDlmshfU2yFgIEkKxSreiF2L0AQfNmheV5D5uDq88X5cXZ8NMePEX4JvzLyIS-hfXmbmLfIURq1H57MB4A2voK2g |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV3JjtQwEC0NgwRc2JewZqThmFG8JLGPTaDVLBoQw0hzi7yKFig9ImmJnhP_wB_yJZSzNHQD0nBNbCvlslPvyeVXAPvSO5Vq4RPNqE84tzTRuUgTwyzXVPIAOkK2xWE-O-avTrKTHSDjXRj8iAZHarpD_LCrT60fFAaCVBC-kBoZicwvwMUMCVYoWjApj35dhaSCjIi3EDkbct23e4dYZJrNWPQHwPx7nuRWbOri0PQavF9b0KWffDpYtvrAnG2JO_6Xidfh6oBK40m_jG7AjqtvwuVyLAZ3C8jRqkao2MybeOHjZ64-W32em3jSF9htYr2Kyx_fvs_it1_nfZWm23A8ffGhnCVDtYVEZTRtE6bwX6NznxWWEF-YLAgYk4J5aSlXPqVOZbbgwiFndoVyEr2fGpsqjSzLGc_uwG69qN09iAWXQqdKaKOR3aVW5lxYRa2gnHnDVAR7aGY17Jam6g7CKRKR8HQwPoKno2-q01544x_t9kbHVTgn4bhD1W6xbCpErsiXgqJdBHd7R65HCuW6JKLLCIoNF68bBNXtzTf1_GOnvp3jqkIWFsH-74th3bHjXEhjSd5BgQjIeZqVgyB7ECJo759jep7ApXfPp9Wbl4evH8AVRHEyXJAk7CHstl-W7hEipVY_7vbGT2GMDVQ |
| 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=Synthesis+of+Benzylic+Alcohols+by+C%E2%80%93H+Oxidation&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.au=Tanwar%2C+Lalita&rft.au=B%C3%B6rgel%2C+Jonas&rft.au=Ritter%2C+Tobias&rft.date=2019-11-13&rft.issn=0002-7863&rft.eissn=1520-5126&rft.volume=141&rft.issue=45&rft.spage=17983&rft.epage=17988&rft_id=info:doi/10.1021%2Fjacs.9b09496&rft.externalDBID=n%2Fa&rft.externalDocID=10_1021_jacs_9b09496 |
| 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 |