Synthesis 2013; 45(6): 817-829
DOI: 10.1055/s-0032-1318119
paper
© Georg Thieme Verlag Stuttgart · New York

Gold and Palladium Combined for the Sonogashira Coupling of Aryl and Heteroaryl Halides

Biswajit Panda
Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India   Fax: +91(3222)282251   eMail: tksr@chem.iitkgp.ernet.in
,
Tarun K. Sarkar*
Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India   Fax: +91(3222)282251   eMail: tksr@chem.iitkgp.ernet.in
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Publikationsverlauf

Received: 05. Dezember 2012

Accepted after revision: 07. Januar 2013

Publikationsdatum:
15. Februar 2013 (online)


Abstract

A highly efficient gold and palladium combined methodology for the Sonogashira coupling of a wide array of electronically and structurally diverse aryl and heteroaryl halides is described. The orthogonal reactivity of the two metals shows high selectivity and extreme functional group tolerance in Sonogashira coupling. A brief mechanistic study reveals that the gold acetylide intermediate enters into the palladium catalytic cycle at the transmetalation step.

Supporting Information