期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 15, 页码 4073-4077出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201800644
关键词
carboxylic acids; catalysis; density functional calculations; palladium; trifluoromethylation
资金
- RWTH Aachen University
- MIWF NRW
- European Research Council [ERC-637993]
- JARA-HPC from RWTH Aachen University [jara0091]
While acid fluorides can readily be made from widely available or biomass-feedstock-derived carboxylic acids, their use as functional groups in metal-catalyzed cross-coupling reactions is rare. This report presents the first demonstration of Pd-catalyzed decarbonylative functionalization of acid fluorides to yield trifluoromethyl arenes (ArCF3). The strategy relies on a Pd/Xantphos catalytic system and the supply of fluoride for transmetalation through intramolecular redistribution to the the Pd center. This strategy eliminated the need for exogenous and detrimental fluoride additives and allows Xantphos to be used in catalytic trifluoromethylations for the first time. Our experimental and computational mechanistic data support a sequence in which transmetalation by R3SiCF3 occurs prior to decarbonylation.
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