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  • Synthesis of gem-difluoroalkenes via nickel-catalyzed allylic defluorinative reductive cross-coupling of trifluoromethyl alkenes with epoxides.

Synthesis of gem-difluoroalkenes via nickel-catalyzed allylic defluorinative reductive cross-coupling of trifluoromethyl alkenes with epoxides.

Organic & biomolecular chemistry (2020-05-08)
Xiao-Yu Lu, Run-Chuang Jiang, Jia-Mei Li, Chuang-Chuang Liu, Qing-Qing Wang, Hai-Pin Zhou
ABSTRACT

A nickel-catalyzed defluorinative reductive cross-coupling of trifluoromethyl alkenes with epoxides has been developed. Various substituted trifluoromethyl alkenes and epoxides were found to be suitable reaction substrates. This reaction enabled C(sp3)-C(sp3) bond construction through allylic defluorinative cross-coupling of trifluoromethyl alkenes under mild reaction conditions. This methodology was highly compatible with various sensitive functional groups, providing access to a diverse array of functionalized gem-difluoroalkene-containing alcohol compounds.

MATERIALS
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Sigma-Aldrich
4,4′,4″-Tri-tert-Butyl-2,2′:6′,2″-terpyridine, 95%