Synthesis 2004(8): 1281-1289  
DOI: 10.1055/s-2004-822354
PAPER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Tetraphosphine Complex: An Efficient Catalyst for the Alkynyl­ation of ortho-Substituted Aryl Bromides

Marie Feuerstein, Florian Berthiol, Henri Doucet*, Maurice Santelli*
Laboratoire de Synthèse Organique, CNRS UMR 6180, Faculté des Sciences de Saint Jérôme, Université d"Aix-Marseille III, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France
Fax: +33(491)983865; e-Mail: henri.doucet@univ.u-3mrs.fr; e-Mail: m.santelli@univ.u-3mrs.fr;
Further Information

Publication History

Received 17 March 2004
Publication Date:
03 May 2004 (online)

Abstract

The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane in combination with [Pd(C3H5)Cl]2 affords a very efficient catalyst for the alkynylation of ortho-substituted aryl bromides. A wide variety of substituents such as phenyl, trifluoromethyl, acetyl, formyl or nitrile, are tolerated. High turnover numbers can be obtained with most of these aryl bromides. The coupling of sterically very congested aryl bromides such as 9-bromoanthracene or 2,4,6-triisopropylbromobenzene also proceeds in good yields.