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Citation: ZHANG Hong, WANG Xin-Ping, YANG Peng-Yu, SHI Ji-Cheng. Suzuki-Miyaura Cross-coupling Reaction Catalyzed by Ferrocene Derivative Coordinated Palladium Complex[J]. Chinese Journal of Applied Chemistry, ;2007, 24(9): 986-990. shu

Suzuki-Miyaura Cross-coupling Reaction Catalyzed by Ferrocene Derivative Coordinated Palladium Complex

1.
a State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024;
2.
b State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian

Corresponding author: WANG Xin-Ping,
Received Date: 11 October 2006
Available Online: 19 April 2007
Fund Project: 国家自然科学基金资助项目(20473089) (20473089)

The coupling reaction of aryl bromide with phenylboronic acid was studied as probe reaction of Suzuki-Miyaura cross-coupling reaction with ferrocene derivatives of monophosphine or bidentate ligand coordinated palladium complex as catalyst. PPFOMe(1-[2-(diphenylphosphino)ferrocenyl]ethyl methyl ether) was most active for the Suzuki-Miyaura cross-coupling reaction when coordinated to palladium. K₂CO₃ was more effective than CsF, and Pd(OAc)₂ was more active than PdCl₂ for the Suzuki-Miyaura cross-coupling reaction between aryl bromides(or its derivatives) and phenylboronic acid. The catalyst made from PPFOMe and Pd(OAc)₂(with a mole ratio of 2:1) was promoted by K₂CO₃, and the yield of 4-methyldiphenyl reached 94% at 110℃ when the reaction of 4-bromotoluene with phenylboronic acid was performed for 1 h. Under the same reaction conditions, all the aryl bromides tested, either electron-poor or electron-rich, led to yields higher than 90%, indicating that ferrocene derivatives of monophosphine coordinated palladium complex are better catalysts for the Suzuki-Miyaura cross-coupling reaction.
- Suzuki-Miyaura cross-coupling reaction,
- ferrocene,
- aryl bromides,
- phenylboronic acid,
- palladium
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