Journal
CHEMICAL COMMUNICATIONS
Volume 53, Issue 79, Pages 10878-10881Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7cc06221d
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Funding
- JST PRESTO [JPMJPR1414]
- JSPS KAKENHI [JP16H04119, JP16H01035, JP17H04875, JP17H05161]
- Grants-in-Aid for Scientific Research [16H01035, 16H04119, 17H04875, 17H05161] Funding Source: KAKEN
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The electrochemical trifluoromethylation and perfluoroalkylation of aromatic compounds mediated by a vitamin B-12 derivative as a cobalt-based catalyst has been developed. The Co(I) species of a vitamin B-12 derivative, prepared by controlled-potential electrolysis at -0.8 V vs. Ag/AgCl in methanol, reacted with RfI (R-f = CF3, n-C3F7, n-C4F9, n-C8F17, and n-C10F21) to form a Co-R-f complex. This complex released an R-f radical under visible light irradiation, which then reacted directly with non-activated (hetero) arenes to form the desired fluoroalkylated molecules through direct C-H functionalization. To our knowledge, this is the first report of a naturally derived vitamin B-12 catalyzed trifluoromethylation and perfluoroalkylation of aromatic compounds as a cobalt-mediated catalyst.
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