Triazole-Based Monophosphine Ligands for Palladium-Catalyzed Cross-Coupling Reactions of Aryl Chlorides

Qian Dai, Wenzhong Gao, Duan Liu, Lea M. Kapes, and Xumu Zhang*
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802
J. Org. Chem., 2006, 71 (10), pp 3928–3934
DOI: 10.1021/jo060321e
Publication Date (Web): April 13, 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.

, xumu@chem.psu.edu

Abstract

Abstract Image

A variety of triazole-based monophosphines (ClickPhos) have been prepared via efficient 1,3-dipolar cycloaddition of readily available azides and acetylenes. Their palladium complexes provided excellent yields in the amination reactions and Suzuki−Miyaura coupling reactions of unactivated aryl chlorides. Ligand 7i, which has a 2,6-dimethoxybenzene moiety, provided good results in Suzuki−Miyaura reaction to form hindered biaryls. A CAChe model for the Pd/7i complex shows that the likelihood of a Pd−arene interaction might be a rationale for its high catalytic reactivity.

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  • Published In Issue May 12, 2006
  • Received February 15, 2006

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