Electrochemical Trifluoromethylalkoxylation of Endocyclic Enamides in Batch and Flow

Author:

Leclercq Elise1,Barakat Waël1,Maazaoui Radhouan2,Penhoat Maël1,Gillaizeau Isabelle2ORCID,Chausset‐Boissarie Laëtitia13ORCID

Affiliation:

1. Lille Univ. CNRS, MSAP, USR 3290 59000 Lille France

2. Université d'Orléans CNRS, UMR 7311, ICOA 45067 Orléans France

3. Normandy Univ. INSA Rouen Normandy UNIROUEN, CNRS COBRA (UMR6014) 76000 Rouen France

Abstract

AbstractA regioselective electrochemical oxytrifluoromethylation of endocyclic enamides is reported. The 1,2‐difunctionalization proceeds under mild conditions and employs the inexpensive bench stable Langlois’ reagent. This multicomponent strategy gives access to a wide range of α,β‐substituted amines by means of various alcohols as nucleophiles in high yields and with good functional group tolerance. In addition, an electrochemically induced C−H trifluoromethylation of enamides has been developed. A continuous flow protocol using a commercial microflow electrochemical reactor was also developed with improved reaction performance and efficiency over traditional batch versions without any supporting electrolyte.

Publisher

Wiley

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