Palladium-catalyzed cross-coupling of 2-haloselenophene with terminal alkynes in the absence of additive

We present herein our results of the Sonogashira coupling reaction of 2-haloselenophenes with terminal alkynes catalyzed by PdCl2(PPh3)(2), under co-catalyst free conditions and establish a new procedure to prepare (2-alkynyl)-selenophenes in good yields. The reaction proceeded cleanly under mild reaction conditions and was performed with propargylic alcohols, protected propargylic alcohols, propargylic amines, as well as alkyl, and aryl alkynes, in the presence of PdCl2(PPh3)(2), Et3N, DMF, and in the absence of any supplementary additives. In addition, by this protocol (2,5-bis-alkynyl)-selenophenes were also obtained, in a one pot procedure, using 2,5-bis-iodoselenofene with an excess of terminal alkynes. (c) 2006 Elsevier Ltd. All rights reserved.