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Copper-Catalyzed Sulfinyl Cross-Coupling Reaction of Sulfinamides

Mengting Kou, Ziqiang Wei, Zhen Li* and Bin Xu*

*Innovative Drug Research Center, School of Medicine, Shanghai University, Shanghai 200444, China, Email: zhenlishushu.edu.cn, xubinshu.edu.cn

M. Kou, Z. Wei, Z. Li, B. Xu, Org. Lett., 2022, 24, 8514-8519.

DOI: 10.1021/acs.orglett.2c03414


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Abstract

A copper-catalyzed sulfinyl cross-coupling reaction of sulfinamides with aldehyde-derived N-tosylhydrazones provides structurally diverse sulfoxides. The reaction offers broad substrate scope and tolerates various functional groups. Moreover, the given sulfinyl cross-coupling reaction could be scaled up to the gram scale and carried out in a one-pot fashion directly from aldehydes.


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proposed mechanism



General procedure:

Sulfinamide (0.3 mmol), N-tosylhydrazone (0.75 mmol), LiOtBu (2.5 equiv), CuI (30 mol%), DMEN (60 mol%) and 1,4-dioxane (1.5 mL) were added in sequence to a Schlenk tube. The mixture was stirred at 50 C in an oil bath for 24 h under N2 atmosphere. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether (1:8-1:2, v/v) as the eluent to afford the desired product.


Key Words

sulfoxides


ID: J54-Y2022