Organic Chemistry Portal

Abstracts

Search:

N-Heterocyclic Carbene-Catalyzed Synthesis of α-Trifluoromethyl Esters

Fabien Gelat, Atanu Patra, Xavier Pannecoucke, Akkattu T. Biju, Thomas Poisson* and Tatiana Besset*

*Normandie Univ., INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France, Email: thomas.poissoninsa-rouen.fr, tatiana.bessetinsa-rouen.fr

F. Gelat, A. Patra, X. Pannecoucke, A. T. Biju, T. Poisson, T. Besset, Org. Lett., 2018, 20, 3897-3901.

DOI: 10.1021/acs.orglett.8b01482 (free Supporting Information)



see article for more reactions

Abstract

A N-heterocyclic carbene (NHC)-catalyzed trifluoromethylation of α-chloro aldehydes provides valuable α-trifluoromethyl ester derivatives in good yields. The unique combination of an electrophilic trifluoromethylation reagent with NHC catalysis was the key for the functionalization of a broad range of substrates. An enantioselective version of this reaction afforded products in moderate yields with good ee values.

see article for more examples



Key Words

trifluoromethylation, organocatalysis, multicomponent reactions


ID: J54-Y2018