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Sulfur-Arylation of Sulfenamides via Ullmann-Type Coupling with (Hetero)aryl Iodides
Nathaniel S Greenwood1, Jonathan A Ellman1
1Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
Abstract:
Sulfur-(hetero)arylation of sulfenamides with commercially abundant (hetero)aryl iodides by Ullmann-type coupling with inexpensive copper(I) iodide as the catalyst is reported. A broad scope of reaction inputs was demonstrated, including both aryl and alkyl sulfenamides and highly sterically hindered aryl and 5- and 6-membered ring heteroaryl iodides. Relevant to many bioactive high oxidation state sulfur compounds, the (hetero)arylation of S-methyl sulfenamides is reported, including for complex aryl iodides. Smiles rearrangement of electron-deficient S-heteroaryl sulfilimines is also disclosed.
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