Premium
Chlorotrifluoromethylation of Terminal Olefins by Atom Transfer‐Type Radical Reaction Catalyzed by Cobalt Complexes
Author(s) -
Maeda Kazuki,
Kurahashi Takuya,
Matsubara Seijiro
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900834
Subject(s) - chemistry , cobalt , catalysis , radical , porphyrin , substrate (aquarium) , derivative (finance) , photochemistry , combinatorial chemistry , polymer chemistry , organic chemistry , oceanography , financial economics , economics , geology
A cobalt porphyrin‐catalyzed chlorotrifluoromethylation reaction of olefins is described. The use of CF 3 SO 2 Cl as the CF 3 radical source and a cobalt catalyst enabled the selective addition of CF 3 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.