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

Nathaniel S. Greenwood and Jonathan A. Ellman*

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

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

DOI: 10.1021/acs.orglett.3c01874



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Abstract

Sulfur-(hetero)arylation of sulfenamides with commercially abundant (hetero)aryl iodides by Ullmann-type coupling with inexpensive copper(I) iodide as the catalyst provides many bioactive high oxidation state sulfur compounds. Smiles rearrangement of electron-deficient S-heteroaryl sulfilimines is also disclosed.


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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.

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.


Key Words

Ullmann coupling, sulfilimines


ID: J54-Y2023