The First General Palladium Catalyst for the Suzuki−Miyaura and Carbonyl Enolate Coupling of Aryl Arenesulfonates

Hanh Nho Nguyen, Xiaohua Huang, and Stephen L. Buchwald*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
J. Am. Chem. Soc., 2003, 125 (39), pp 11818–11819
DOI: 10.1021/ja036947t
Publication Date (Web): September 9, 2003
Copyright © 2003 American Chemical Society
*

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

, sbuchwal@mit.edu

Abstract

Abstract Image

The first general method for the palladium-catalyzed Suzuki−Miyaura and carbonyl enolate coupling of unactivated aryl arenesulfonates was developed utilizing XPhos, 1, and Pd(OAc)2. This is of significant interest because aryl tosylates and aryl benzenesulfonates are more easily handled and considerably less expensive than aryl triflates. This catalyst system effects the coupling of a variety of aryl, heteroaryl, and extremely hindered arylboronic acids with different aryl tosylates, under mild conditions. The same catalyst was employed in the first carbonyl enolate coupling of aryl arensulfonates.

View: Full Text HTML | Hi-Res PDF

Tools

History

  • Published In Issue October 01, 2003
  • Received June 27, 2003

Recommend & Share

Related Content

Other ACS content by these authors: