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Achiral Pyridine Ligand‐Enabled Enantioselective Radical Oxytrifluoromethylation of Alkenes with Alcohols
Author(s) -
Cheng YongFeng,
Dong XiaoYang,
Gu QiangShuai,
Yu ZhangLong,
Liu XinYuan
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201702925
Subject(s) - stereocenter , chemistry , enantioselective synthesis , pyridine , ligand (biochemistry) , combinatorial chemistry , asymmetric induction , radical , substrate (aquarium) , trifluoromethyl , catalysis , organic chemistry , biochemistry , oceanography , receptor , alkyl , geology
A conceptually novel strategy with achiral pyridine as the ancillary ligand to stabilize high‐valent copper species for the first asymmetric radical oxytrifluoromethylation of alkenes with alcohols under Cu I /phosphoric acid dual‐catalysis has been developed. The transformation features mild reaction conditions, a remarkably broad substrate scope and excellent functional group tolerance, offering an efficient approach to a wide range of trifluoromethyl‐substituted tetrahydrofurans bearing an α‐tertiary stereocenter with excellent enantioselectivity. Mechanistic studies support the presumed role of the achiral pyridine as a coordinative ligand on copper metal to stabilize the key transient reaction species involved in the asymmetric induction process.