Practical and Efficient Suzuki−Miyaura Cross-Coupling of 2-Iodocycloenones with Arylboronic Acids Catalyzed by Recyclable Pd(0)/C

François-Xavier Felpin
Universit Bordeaux-I, Laboratoire de Chimie Organique et Organomtallique, 351 Cours de la Libration, 33405 Talence Cedex, France fx.felpin@lcoo.u-bordeaux1.fr
J. Org. Chem., 2005, 70 (21), pp 8575–8578
DOI: 10.1021/jo051501b
Publication Date (Web): September 14, 2005
Copyright © 2005 American Chemical Society

 This paper is dedicated with respect to my mentors Jacques Lebreton (Université de Nantes) and Robert S. Coleman (Ohio State University).

Abstract

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The first Suzuki−Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by 10% Pd(0)/C is described as an interesting alternative to classical homogeneous conditions. Most of the substrate reacted under mild condition at 25 °C under air in aqueous DME. The conditions described tolerate a wide range of iodoenones and boronic acids. Notably, the procedure features inexpensive reagents and solvents with low toxicity rendering the method environmentally benign. Additionally 10% Pd(0)/C could be recovered and efficiently reused at least five times without significant alteration of the yields of the cross-coupled product.

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History

  • Published In Issue October 14, 2005
  • Received July 19, 2005

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