A General and Long-Lived Catalyst for the Palladium-Catalyzed Coupling of Aryl Halides with Thiols

Manuel A. Fernández-Rodríguez, Qilong Shen, and John F. Hartwig*
Department of Chemistry, Yale University, PO Box 208107 New Haven, Connecticut 06520-8107
J. Am. Chem. Soc., 2006, 128 (7), pp 2180–2181
DOI: 10.1021/ja0580340
Publication Date (Web): January 31, 2006
Copyright © 2006 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.

, john.hartwig@yale.edu

Abstract

Abstract Image

A general catalytic system for the coupling of aryl halides and sulfonates with thiols based on the use of the CyPF-t-Bu ligand (1) is reported. The reactions catalyzed by complexes of 1 occur in excellent yields with broad scope and exhibit extraordinary turnover numbers and high tolerance of functional groups. Turnover numbers usually exceed those of previous catalysts by 2 or 3 orders of magnitude. In addition, the reactions of aryl tosylates with alkane thiols to form aryl sulfides are reported for the first time. Finally, the synthesis of a diarylsulfide from two bromoarenes was accomplished using a hydrogen sulfide surrogate.

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History

  • Published In Issue February 22, 2006
  • Received November 25, 2005

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