4.8 Article

NHC-Catalyzed Electrophilic Trifluoromethylation: Efficient Synthesis of gamma-Trifluoromethyl alpha,beta-Unsaturated Esters

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 37, Pages 12097-12101

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201806674

Keywords

fluorine; N-heterocyclic carbenes; organocatalysis; regioselectivity; trifluoromethylation

Funding

  1. Shenzhen STIC [JCYJ20160229205441091]
  2. Hong Kong RGC [16304115, 16302617, 16311616]

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Described herein is a highly regioselective and efficient N-heterocyclic-carbene-catalyzed gamma-trifluoromethylation of vinylogous enolates. Control experiments and DFT calculations provided important insight into the reaction mechanism.

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