Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 39, Pages 11986-11989Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201706868
Keywords
asymmetric catalysis; cross-coupling; fluorine; nickel; trifluoromethoxy groups
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Funding
- National Natural Science Foundation of China [21625206, 21632009, 21372247, 21572258, 21572259, 21421002]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
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Trifluoromethoxy-substituted stereogenic centers can be constructed with high enantioselectivity by a nickel-catalyzed Suzuki-Miyaura coupling of readily available alpha-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.
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