Pd-Complex Catalyzed Suzuki Cross-Coupling Reaction of Brominated Salicylaldehyde with Pyridylboronic Acid

doi:10.6023/cjoc201407024

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (12): 2471-2477.DOI: 10.6023/cjoc201407024 Previous Articles Next Articles

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钯催化溴代水杨醛与吡啶硼酸的Suzuki交叉偶联反应

王碧玉^a, 倪沛钟^a, 范吉理^a, 郑辉东^a, 赵素英^a, 白正帅^a,b

a. 福州大学石油化工学院福州 350108;
b. 能源与环境光催化国家重点实验室福州 350002

收稿日期:2014-07-12 修回日期:2014-08-17 发布日期:2014-09-09
通讯作者: 白正帅 E-mail:baizs@fzu.edu.cn
基金资助:
国家基础科学人才培养基金(No.J1103303)和福州大学科研启动基金(No.XRC-1305)资助项目.

Pd-Complex Catalyzed Suzuki Cross-Coupling Reaction of Brominated Salicylaldehyde with Pyridylboronic Acid

Wang Biyu^a, Ni Peizhong^a, Fan Jili^a, Zheng Huidong^a, Zhao Suying^a, Bai Zhengshuai^a,b

a. School of Chemical Engineering, Fuzhou University, Fuzhou 350108;
b. State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou 350002

Received:2014-07-12 Revised:2014-08-17 Published:2014-09-09
Supported by:
Project supported by the National Natural Science Fundation of China (No. J1103303) and the Research Fund of Fuzhou University (No. XRC-1305).

1. Pd-Complex Catalyzed Suzuki Cross-Coupling Reaction of Brominated Salicylaldehyde with Pyridylboronic Acid.PDF(1028KB)

Abstract

The synthesis of 3-tert-butyl-2-hydroxy-5-(pyridin-4-yl)benzaldehyde by Suzuki cross coupling reaction of 5-bromo-3-tert-butyl-2-hydroxybenzaldehyde with pyridin-4-ylboronic acid was studied by using different catalysts [Pd(dppf)₂Cl₂, Pd(OAc)₂ and Pd(PPh₃)₄], bases (Na₂CO₃, NaHCO₃, K₂CO₃, K₃PO₄, Cs₂CO₃ and CsF) and solvents (DME/H₂O, DMF/H₂O and dioxane/H₂O) under different temperature of 70, 80 and 100 ℃. A compatible method was developed for the coupling reaction of arylboronic acids (having electron donating or withdrawing group) with aryl bromides (having electron withdrawing group). Under the condition of Pd(PPh₃)₄, K₂CO₃, dioxane/H₂O (V:V=4:1), 80 ℃, the yield is excellent (97%) and the product separation is easy. The compatibility for aryl bromides with electron donating group is moderate.

Key words: Suzuki cross coupling reaction, pyridylboronic acid, aryl bromide, catalytic mechanism

Cite this article

Wang Biyu, Ni Peizhong, Fan Jili, Zheng Huidong, Zhao Suying, Bai Zhengshuai. Pd-Complex Catalyzed Suzuki Cross-Coupling Reaction of Brominated Salicylaldehyde with Pyridylboronic Acid[J]. Chin. J. Org. Chem., 2014, 34(12): 2471-2477.

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钯催化溴代水杨醛与吡啶硼酸的Suzuki交叉偶联反应

Pd-Complex Catalyzed Suzuki Cross-Coupling Reaction of Brominated Salicylaldehyde with Pyridylboronic Acid

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