Synthesis 2007(3): 393-399  
DOI: 10.1055/s-2007-965883
PAPER
© Georg Thieme Verlag Stuttgart · New York

Pd(N,N-Dimethyl β-alaninate)2 as a High-Turnover-Number, Phosphine-Free Catalyst for the Suzuki Reaction

Xin Cui, Tian Qin, Jia-Rui Wang, Lei Liu*, Qing-Xiang Guo*
Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China
e-Mail: leiliu@ustc.edu; e-Mail: qxguo@ustc.edu.cn;
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Publikationsverlauf

Received 25 August 2006
Publikationsdatum:
12. Januar 2007 (online)

Abstract

A novel crystalline, air- and moisture-stable Pd salt, Pd(N,N-dimethyl β-alaninate)2, was synthesized. This salt was demonstrated­ to constitute a low-priced, phosphine-free, yet high-turnover-number (TON = 104) catalyst for the Suzuki reactions of various aryl bromides and iodides under mild and simple reaction conditions. Moreover, it was observed that the presence of an olefin could dramatically hamper the Suzuki reaction.

3

Practically speaking, any catalyst displaying a turnover number (TON) of greater than 103, i.e. a catalyst that can lead to complete conversion of starting materials at a load of 0.1% mol, will be considered as a high-turnover-number catalyst.