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Chemoselective Acylation of Primary Amines and Amides with Potassium Acyltrifluoroborates under Acidic Conditions

Alberto Osuna Gálvez, Cédric P. Schaack, Hidetoshi Noda and Jeffrey W. Bode*

*Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich, 8093 Zürich, Switzerland, Email: bodeorg.chem.ethz.ch

A. O. Gálvez, C. P. Schaack, H. Noda, J. W. Bode, J. Am. Chem. Soc., 2017, 139, 1826-1829.

DOI: 10.1021/jacs.7b00059 (free Supporting Information)


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Abstract

An amide formation using primary amines and potassium acyltrifluoroborates, that proceeds rapidly in water, is promoted by simple chlorinating agents. The reaction is fast at acidic pH and tolerates alcohols, carboxylic acids, and even secondary amines in the substrates. It is applicable to the (late-stage) functionalization of primary amides, sulfonamides, and other N-functional groups that typically resist classical acylations.

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Key Words

amides


ID: J48-Y2017