Simultaneous Preparation of Sulfides/Selenides and Sulfones via Synergistic Nickel-Catalyzed Reductive Coupling and S_N2 Reaction

Ji-Min Cao, Wei-Chen Zhu, Xin-Yu Liu, Weidong Rao, Shu-Su Shen, Dao-peng Sheng, Shun-Yi Wang*

*College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China, Email: shunyisuda.edu.cn

J.-M. Cao, W.-C. Zhu, X.-Y. Liu, W. Rao, S.-S. Shen, D.-p. Sheng, S.-Y. Wang, Org. Lett., 2023, 25, 9207-9212.

DOI: 10.1021/acs.orglett.3c03777

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Abstract

Sulfides/selenides and sulfones can be obtained simultaneously using a nickel-catalyzed reductive coupling and S_N2 synergistic reaction of allyl/benzyl bromides with thiosulfonates/selenosulfonates. The strategy offers excellent step economy, mild reaction conditions, broad functional group compatibility, and excellent yields.

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proposed mechanism

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Key Words

allyl sulfones, benzyl sulfones, allyl sulfides, benzyl sulfides, manganese

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ID: J54-Y2023