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Enantioselective Construction of Trifluoromethoxylated Stereogenic Centers by a Nickel‐Catalyzed Asymmetric Suzuki–Miyaura Coupling of Secondary Benzyl Bromides
Author(s) -
Huang Weichen,
Wan Xiaolong,
Shen Qilong
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201706868
Subject(s) - stereocenter , enantioselective synthesis , pinacol , aryl , chemistry , trifluoromethyl , catalysis , ketone , bromide , organic chemistry , combinatorial chemistry , alkyl
Trifluoromethoxy‐substituted stereogenic centers can be constructed with high enantioselectivity by a nickel‐catalyzed Suzuki–Miyaura coupling of readily available α‐bromobenzyl trifluoromethyl ethers with a variety of aryl pinacol boronates. The coupling proceeds under mild reaction conditions, and a variety of common functional groups, such as fluoride, chloride, bromide, ester, enolizable ketone, nitro, cyano, amino, and vinyl moieties, were well tolerated. Furthermore, the reaction can be easily scaled up to gram quantities without a decrease in enantioselectivity.