Palladium-Catalyzed Ligand-Free Suzuki Reaction of Potassium Aryltrifluoroborates in Aqueous Ethanol

doi:10.6023/cjoc201601001

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (6): 1341-1350.DOI: 10.6023/cjoc201601001 Previous Articles Next Articles

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无配体钯催化乙醇水溶液中芳基三氟硼酸钾的Suzuki反应

李新民, 刘春, 刘超, 金子林

大连理工大学精细化工国家重点实验室大连 116012

收稿日期:2016-01-02 修回日期:2016-01-20 发布日期:2016-02-24
通讯作者: 刘春 E-mail:cliu@dlut.edu.cn
基金资助:
国家自然科学基金(Nos.21276043,21421005)及大连理工大学离退休科研基金(No.DUTTX2015102)资助项目.

Palladium-Catalyzed Ligand-Free Suzuki Reaction of Potassium Aryltrifluoroborates in Aqueous Ethanol

Li Xinmin, Liu Chun, Liu Chao, Jin Zilin

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012

Received:2016-01-02 Revised:2016-01-20 Published:2016-02-24
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21276043, 21421005) and the Research Foundation of Dalian University of Technology for Retired Professors (No. DUTTX2015102).

1. Palladium-Catalyzed Ligand-Free Suzuki Reaction of Potassium Aryltrifluoroborates in Aqueous Ethanol.PDF(7923KB)

Abstract

A simple and ligand-free protocol has been developed for the Pd(OAc)₂-catalyzed Suzuki reaction of potassium aryltrifluoroborates in aqueous ethanol under air. In the presence of Pd(OAc)₂ and 1 equiv. of K₂CO₃, aryl or heteroaryl halides coupled with various potassium aryltrifluoroborates smoothly to afford the products in high yields with the highest turnover frequency (TOF) up to 4656 h^-1, and a series of triphenylamine derivatives were prepared efficiently in this system. In addition, the active catalyst was proved to be the in situ-generated palladium nanoparticles according to TEM analysis and mercury-poisoning test.

Key words: palladium, ligand-free, Suzuki reaction, potassium aryltrifluoroborates, aqueous ethanol

Cite this article

Li Xinmin, Liu Chun, Liu Chao, Jin Zilin. Palladium-Catalyzed Ligand-Free Suzuki Reaction of Potassium Aryltrifluoroborates in Aqueous Ethanol[J]. Chin. J. Org. Chem., 2016, 36(6): 1341-1350.

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无配体钯催化乙醇水溶液中芳基三氟硼酸钾的Suzuki反应

Palladium-Catalyzed Ligand-Free Suzuki Reaction of Potassium Aryltrifluoroborates in Aqueous Ethanol

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