N,N-Dimethyl-β-alanine as an Inexpensive and Efficient Ligand for Palladium-Catalyzed Heck Reaction

Xin Cui, Zhe Li, Chuan-Zhou Tao, Yu Xu, Juan Li, Lei Liu,* and Qing-Xiang Guo*;
Department of Chemistry, University of Science and Technology of China, Hefei 230026, China
Org. Lett., 2006, 8 (12), pp 2467–2470
DOI: 10.1021/ol060585n
Publication Date (Web): May 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.

, leiliu@ustc.edu, ; , qxguo@ustc.edu.cn

Abstract

Abstract Image

N,N-Dimethyl-β-alanine was found to be a more powerful phosphine-free ligand than the previously reported ligand, N,N-dimethylglycine, in the Pd-catalyzed Heck reaction for a variety of aryl bromides, aryl iodides, and activated aryl chlorides with a practical turnover number of 103. Both kinetic and theoretical studies suggested that N,N-dimethyl-β-alanine led to faster oxidative addition of an aryl halide to Pd than N,N-dimethylglycine.

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History

  • Published In Issue June 08, 2006
  • Received March 9, 2006

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