4.5 Article

Chlorotrifluoromethylation of Terminal Olefins by Atom Transfer-Type Radical Reaction Catalyzed by Cobalt Complexes

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

  1. ACT-C from the JST (Japan)
  2. MEXT (Japan) [18H04253, 17KT0006, 15H05845, 15H03809]
  3. Grants-in-Aid for Scientific Research [15H05845, 15H03809, 17KT0006, 18H04253] Funding Source: KAKEN

向作者/读者索取更多资源

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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