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Amides in One Pot from Carboxylic Acids and Amines via Sulfinylamides

Jianfei Bai, Bartosz K. Zambroń and Pierre Vogel*

*Laboratoire de Glycochimie et de Synthèse Asymétrique, Swiss Federal Institute of Technology (EPFL), Batochime, CH 1015 Lausanne, Switzerland, Email: Pierre.Vogelepfl.ch

J. Bai, B. K. Zembrón, P. Vogel, Org. Lett., 2014, 16, 604-607.

DOI: 10.1021/ol403508j (free Supporting Information)


Abstract

The use of sulfinylamides generated in situ by the reaction of pure amines with prop-2-ene-1-sulfinyl chloride enables an efficient amidification of carboxylic acids. The method allows the conversion of aliphatic acids, including pivalic acid, aromatic acids, and primary and secondary amines and tolerates acids bearing unprotected alcohol, phenol, and ketone moieties without α-epimerization.


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Key Words

amides


ID: J54-Y2014