Palladium-Catalyzed Nucleophilic Benzylic Substitutions of Benzylic Esters

Ryoichi Kuwano,* Yutaka Kondo, and Yosuke Matsuyama
Department of Chemistry, Graduate School of Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan
J. Am. Chem. Soc., 2003, 125 (40), pp 12104–12105
DOI: 10.1021/ja037735z
Publication Date (Web): September 12, 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.

, rkuwascc@mbox.nc.kyushu-u.ac.jp

Abstract

Abstract Image

A palladium complex generated in situ from [Pd(η3-C3H5)(cod)]BF4 and DPPF is a good catalyst for benzylic alkylation of benzyl methyl carbonate with the carbanion of dimethyl malonates. The catalytic reaction is applicable to a wide range of the benzylations of benzylic esters with malonates. The catalytic activity was heavily affected by the bite angle of the bidentate phosphine ligand on palladium. DPEphos ligand is superior to DPPF in the case of palladium-catalyzed benzylic amination of benzylic esters.

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History

  • Published In Issue October 08, 2003
  • Received August 4, 2003

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