Issue 1, 2016

Triphenylphosphine promoted regio and stereoselective α-halogenation of ynamides

Abstract

In this study, we demonstrate metal free regio- and stereoselective α-halogenation (Cl, Br and I) of ynamides. The halogenation of ynamides in the presence of PPh3 and CCl4, CBr4 or CHI3 in moist CH2Cl2 at room temperature provides good-to-excellent yields of a wide variety of stable (E)-α-haloenamides; thus, the reaction has a broad scope. Chlorination of ynamides at room temperature is particularly notable. The sequential one pot α-iodination and alkynylation of ynamides provide synthetically useful amidoenynes. The chlorination of 3-acetoxy ynamide delivers 3-acetoxy-α-chloro enamide without the migratory-assistance of the acetoxy moiety.

Graphical abstract: Triphenylphosphine promoted regio and stereoselective α-halogenation of ynamides

Supplementary files

Article information

Article type
Research Article
Submitted
03 Nov 2015
Accepted
27 Nov 2015
First published
30 Nov 2015

Org. Chem. Front., 2016,3, 110-115

Author version available

Triphenylphosphine promoted regio and stereoselective α-halogenation of ynamides

B. Prabagar, S. Nayak, R. K. Mallick, R. Prasad and A. K. Sahoo, Org. Chem. Front., 2016, 3, 110 DOI: 10.1039/C5QO00345H

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