Copper-Catalyzed Cross-Coupling of Alkyl and Phosphorus Radicals for C(sp³)-P Bond Formation

Cheng-Kun Li, Ze-Kun Tao, Adedamola Shoberu, Wei Zhang* and Jian-Ping Zou*

*University of Massachusetts Boston, Boston, Massachusetts 02125, United States; Soochow University, Suzhou, Jiangsu 215123, China, Email: wei2.zhangumb.edu, jpzousuda.edu.cn

C.-K. Li, Z.-K. Tao, A. Shoberu, W. Zhang, J.-P. Zou, Org. Lett., 2022, 24, 6083-6087.

DOI: 10.1021/acs.orglett.2c02454

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Abstract

Diacyl peroxides, generated in situ from aliphatic acids and H₂O₂, serve as a source for alkyl radicals and also an initiator for the generation of phosphorus radicals from H-P(O) compounds. A subsequent CuI-catalyzed cross-coupling of alkyl- and phosphorus-centered radicals provides alkylated phosphorous compounds in good yields.

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proposed mechanism

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Key Words

phosphine oxides, phosphonates, peroxides

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ID: J54-Y2022