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

Fabien Gelat (1) , A. Patra (2) , Xavier Pannecoucke (1) , A.T. Biju , Thomas Poisson (1) , Tatiana Besset (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 PPSM - Laboratoire de Photophysique et Photochimie Supramoléculaires et Macromoléculaires

The N-heterocyclic carbene (NHC)-catalyzed trifluoromethylation of α-chloro aldehydes was developed, allowing straightforward access to valuable α-trifluoromethyl ester derivatives. The unique combination of an electrophilic trifluoromethylation reagent with NHC catalysis was the key for the functionalization of a broad range of α-chloro aldehydes, and the products are formed in moderate to good yields. Investigations of the enantioselective version of this reaction afforded the enantioenriched products in moderate yields with good ee values.

Domains: Chemical Sciences

Fabien Gelat, A. Patra, Xavier Pannecoucke, A.T. Biju, Thomas Poisson, et al.. N-Heterocyclic Carbene-Catalyzed Synthesis of α-Trifluoromethyl Esters. Organic Letters, 2018, 20 (13), pp.3897-3901. ⟨10.1021/acs.orglett.8b01482⟩. ⟨hal-02024497⟩