Electrochemical Trifluoromethylalkoxylation of Endocyclic Enamides in Batch and Flow

A 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 m...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-07, Vol.366 (13), p.2919-2925
Main Authors: Leclercq, Elise, Barakat, Waël, Maazaoui, Radhouan, Penhoat, Maël, Gillaizeau, Isabelle, Chausset‐Boissarie, Laëtitia
Format: Article
Language:English
Subjects:
1,2-difunctionalization
Alcohols
Amines
Chemical reactors
Chemical Sciences
Continuous flow
electrochemical
enamides
flow cell
Functional groups
Nucleophiles
Reagents
trifluoromethylation
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Summary:A 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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202301485