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

Andrew T. Champlin and Jonathan A. Ellman*

*Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States, Email: jonathan.ellmanyale.edu

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

DOI: 10.1021/acs.joc.3c00750



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Abstract

Sulfur alkylation of N-acyl sulfenamides with alkyl halides provides sulfilimines in good yields. A broad scope was established with a variety of aryl and alkyl sulfenamides, including for different N-acyl groups. A proof-of-concept asymmetric phase-transfer alkylation was also demonstrated.


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

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

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

sulfilimines


ID: J42-Y2023