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Cu(II)/Proline-Catalyzed Reductive Coupling of Sulfuryl Chloride and P(O)-H for P-S-C Bond Formation

Xinghua Zhang*, Dungai Wang, Duo An, Boshi Han, Xiang Song, Liang Li, Gaoqi Zhang and Lixian Wang*

*School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Hai-Quan Road, Shanghai 201418, China, Email:,

X. Zhang, D. Wang, D. An, B. Han, X. Song, L. Li, G. Zhang, L. Wang, J. Org. Chem., 2018, 83, 1532-1537.

DOI: 10.1021/acs.joc.7b02608


Using L-proline as the ligand for a Cu-catalyzed coupling of sulfuryl chloride with P(O)-H compounds decreased the precatalyst loading, broadened the substrate scope and greatly promoted the efficiency of the coupling reaction. Moreover, gram-scale preparation, easy-to handle and recyclable catalyst featured this transformation.

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proposed mechanism

Key Words

P-S Bond Formation, Phosphorothioates

ID: J42-Y2018