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Copper-Catalyzed P-Arylation via Direct Coupling of Diaryliodonium Salts with Phosphorus Nucleophiles at Room Temperature

Jian Xu, Pengbo Zhang, Yuzhen Gao, Yiyin Chen, Guo Tang* and Yufen Zhao

*Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, China, Email: t12g21xmu.edu.cn

J. Xu, P. Zhang, Y. Gao, Y. Chen, G. Tang, Y. Zhao, J. Org. Chem., 2013, 78, 8176-8183.

DOI: 10.1021/jo4012199 (free Supporting Information)


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Abstract

A copper-catalyzed reaction of phosphorus nucleophiles with diaryliodonium salts at room temperature delivers products of a P-C bond formation in high yields within a short reaction time of 10 min. The method can be easily adapted to large-scale preparations. With unsymmetrical iodonium salts, nucleophilic substitution occurs preferentially on the sterically hindered aromatic ring or the more electron-deficient ring.

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Key Words

Phosphine Oxides, Phosphonates


ID: J42-Y2013