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Synthesis 2006(9): 1465-1469  
DOI: 10.1055/s-2006-926424
PAPER
© Georg Thieme Verlag Stuttgart · New York

Nickel(0)/Tetra-n-butylammonium Bromide (TBAB) Catalyzed Suzuki-Miyaura Reaction

Erli Youa, Pinhua Lia, Lei Wang*a,b
a Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, P. R. of China
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(561)3090518; e-Mail: leiwang@hbcnc.edu.cn;
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Publication History

Received 7 November 2005
Publication Date:
07 April 2006 (online)

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Abstract

A nickel(0)/tetra-n-butylammonium bromide (TBAB) catalyzed Suzuki-Miyaura reaction of aryl iodides and bromides with organoboronic acids was developed under phosphine-free reaction conditions. The reaction involved the use of ethanol as solvent, sodium carbonate as base, and nickel metal colloids stabilized by TBAB as catalyst. For activated aryl chlorides, excellent yields of the products were isolated when PPh3 was added to the reaction. Furthermore, the nickel metal could be recovered and recycled for six consecutive trials without significant loss of its reactivity.

Key words

nickel(0) metal colloids - Suzuki-Miyaura reaction - tetra-n-butylammonium bromide (TBAB)