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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
Abstract : 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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02024497
Contributor : Madeleine Roux-Merlin <>
Submitted on : Tuesday, February 19, 2019 - 11:09:38 AM
Last modification on : Friday, April 30, 2021 - 10:21:00 AM

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COBRA | COMUE-NORMANDIE | CNRS | UNIROUEN | INSA-ROUEN | ENS-CACHAN | INC-CNRS | INSA-GROUPE | ENSICAEN | UNILEHAVRE | UNICAEN | ENS-PARIS-SACLAY | GS-CHIMIE

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

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