Assembly of (hetero)aryl sulfilimines via copper-catalyzed enantioselective S-arylation of sulfenamides with (hetero)aryl Iodides

Mingchuang He, Rongxing Zhang, Tongkun Wang, Xiao-Song Xue () and Dawei Ma ()
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Mingchuang He: East China Normal University
Rongxing Zhang: Southern University of Science and Technology (SUSTech)
Tongkun Wang: University of Chinese Academy of Sciences, Chinese Academy of Science
Xiao-Song Xue: University of Chinese Academy of Sciences, Chinese Academy of Science
Dawei Ma: Southern University of Science and Technology (SUSTech)

Nature Communications, 2025, vol. 16, issue 1, 1-8

Abstract: Abstract The (hetero)aryl sulfoximines are important structures for developing bioactive molecules, whose synthesis relies on oxidation of (hetero)aryl sulfilimines. However, asymmetric approaches for assembling (hetero)aryl sulfilimines are still rare. Here we show that combination of CuI and NOBIN-derived amide ligands offers an effective catalytic system for enantioselective coupling of (hetero)aryl iodides with sulfenamides. A large number of functional groups and heterocycles are tolerated under the coupling conditions, providing a powerful approach for diverse synthesis of enantioenriched (hetero)aryl sulfilimines. The efficiency of the coupling reaction is highly dependent on the electronic nature of (hetero)aryl iodides and sulfenamides. Both (hetero)aryl- and some bulky alkyl-substituted sulfenamides give excellent enantioselectivities, while sulfenamides with smaller alkyl substituents lead to the formation of the (hetero)aryl sulfilimines with moderate enantioselectivities. Density functional theory (DFT) calculations reveal that proper steric repulsions in the transition states of the intramolecular SNAr reaction are crucial for achieving desirable enantioselectivity.

Date: 2025
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DOI: 10.1038/s41467-025-57474-6

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