(IPr)Pd(acac)Cl:  An Easily Synthesized, Efficient, and Versatile Precatalyst for C−N and C−C Bond Formation

Nicolas Marion,† Elise C. Ecarnot,†‡ Oscar Navarro,† Dino Amoroso,§ Andrew Bell,§ and Steven P. Nolan*†
Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148, and Promerus LLC, 9921 Brecksville Road, Brecksville, Ohio 44141-3289
J. Org. Chem., 2006, 71 (10), pp 3816–3821
DOI: 10.1021/jo060190h
Publication Date (Web): April 11, 2006
Copyright © 2006 American Chemical Society
†

 University of New Orleans.

,
‡

 Visiting student from Ecole Nationale Supérieure de Techniques Avancées (ENSTA), Paris, France.

,
§

 Promerus LLC.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, snolan@uno.edu

Abstract

Abstract Image

A very straightforward synthesis of (IPr)Pd(acac)Cl from two commercially available starting materials, Pd(acac)2 and IPr·HCl [acac = acetylacetonate; IPr = N,N‘-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], has been developed. The resulting complex, (IPr)Pd(acac)Cl (1), has proven to be a highly active PdII precatalyst in the Buchwald−Hartwig and the α-ketone arylation reactions. A wide range of substrates has been screened, including unactivated, sterically hindered, and heterocyclic aryl chlorides.

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History

  • Published In Issue May 12, 2006
  • Received January 28, 2006

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