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Sulfur-Arylation of Sulfenamides via Chan-Lam Coupling with Boronic Acids: Access to High Oxidation State Sulfur Pharmacophores

Nathaniel S. Greenwood and Jonathan A. Ellman*

*Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States, Email:

N. S. Greenwood, J. A. Ellman, Org. Lett., 2023, 25, 2830-2834.

DOI: 10.1021/acs.orglett.3c00779

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A Chan-Lam-type sulfur-arylation of sulfenamides with commercially abundant boronic acids provides sulfilimines. This coupling reaction converts a broad scope of readily accessible aryl and alkyl sulfenamide and boronic acid substrates. Derivatization of the sulfilimine products enables access to medicinally relevant sulfoximines and sulfondiimines.

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Preparation of Sulfilimines by Sulfur-Alkylation of N-Acyl Sulfenamides with Alkyl Halides

A. T. Champlin, J. A. Ellman, J. Org. Chem., 2023, 88, 7607-7614.

Sulfur-Arylation of Sulfenamides via Ullmann-Type Coupling with (Hetero)aryl Iodides

N. S. Greenwood, J. A. Ellman, Org. Lett., 2023, 25, 4759-4764.

Key Words

Chan-Lam coupling, sulfilimines

ID: J54-Y2023