Synlett 2002(2): 0328-0330
DOI: 10.1055/s-2002-19769
LETTER
© Georg Thieme Verlag Stuttgart · New York

In Situ Generation of 1-Propyne: A Useful Introduction of 1-Propyne on Unsaturated Halogenated Compounds through the Sonogashira Reaction

Estelle Abraham, Jean Suffert*
Laboratoire de Pharmacochimie de la Communication Cellulaire (UMR 7081 CNRS/ULP), Faculté de Pharmacie, 74 route du Rhin 67401 Illkirch-Cedex, France
Fax: +33(390)244310; e-Mail: jeansu@aspirine.u-strasbg.fr;
Further Information

Publication History

Received 6 November 2001
Publication Date:
02 February 2007 (online)

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Abstract

Reaction of (E/Z)-1-bromopropene with exactly 1.42 equivalents of nBuLi followed by addition of water produces in situ a THF solution of propyne. Addition of a vinylic or aromatic halogenated substrates, Pd(PPh3)2Cl2, CuI and an amine to this solution give high yield of the corresponding coupling product bearing a propyne moiety. This practical procedure avoids the use of expensive and inflammable propyne gas which need a special apparatus for bubbling it into the reaction flask.