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: zhenlishu
shu.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
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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
ID: J54-Y2022
