期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2019, 期 28, 页码 4613-4616出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900834
关键词
Atom transfer; Cobalt catalysis; Trifluoromethylation; Olefins; Radical reactions
资金
- ACT-C from the JST (Japan)
- MEXT (Japan) [18H04253, 17KT0006, 15H05845, 15H03809]
- Grants-in-Aid for Scientific Research [15H05845, 15H03809, 17KT0006, 18H04253] Funding Source: KAKEN
A cobalt porphyrin-catalyzed chlorotrifluoromethylation reaction of olefins is described. The use of CF3SO2Cl as the CF3 radical source and a cobalt catalyst enabled the selective addition of CF3 radicals under thermal conditions. Various functional groups such as esters and Ar-X moieties, which can be reactive with low valent transition metal catalysts, were well-tolerated in this catalytic process. A highly functionalized alkaloid derivative was also tolerated as a substrate. As a demonstration of the bio-inspired catalytic system, catalytic usage of vitamin B-12, which is the commercially available form of the natural cobalt porphyrinoid, was employed, and diastereoselective chlorotrifluoromethylation of the alkaloid molecule was achieved.
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