Chemoselective α-Trifluoroacetylation of Amides Using Highly Electrophilic Trifluoroacetic Anhydrides and 2,4,6-Collidine.

Org Lett

Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho Midori-ku, Yokohama 226-8501, Japan.

Published: December 2023


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Article Abstract

Chemoselective α-acylation of tertiary amides proceeded with highly electrophilic acid anhydrides and weak bases under mild conditions. β-Ketoamides containing trifluoroacetyl or perfluoroacyl groups were selectively obtained even in the presence of other functional groups such as ketone, ester, etc. Density functional theory calculations suggest that 1-acyloxyenamine is the key intermediate for the chemoselective α-acylation.

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http://dx.doi.org/10.1021/acs.orglett.3c03719DOI Listing

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