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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:

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

DOI: 10.1021/acs.joc.3c00750

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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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Key Words


ID: J42-Y2023