Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions

Zhengjiang Fu, Zhaojie Li, Yuanyuan Song, Ruchun Yang, Yanzhu Liu and Hu Cai*

*College of Chemistry, Nanchang University, Nanchang 330031, China, Email: caihuncu.edu.cn

Z. Fu, Z. Li, Y. Song, R. Yang, Y. Liu, H. Cai, J. Org. Chem., 2016, 81, 2794-2803.

DOI: 10.1021/acs.joc.5b02873

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Abstract

Cu(I) as promoter enables simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids under aerobic conditions. For the conversion of electron-rich benzoic acids, Pd(II) must be used as catalyst. The method provides aryl halides (-I, Br, and Cl) in the presence of readily available halogen sources CuX (X = I, Br, Cl) and benzonitriles in the presence of nontoxic and low-cost K₄Fe(CN)₆.

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Key Words

iodination, oxygen

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ID: J42-Y2016