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

Nathaniel S Greenwood, Jonathan A Ellman

Organic letters 2023 Jun 30

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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.

Citation

Nathaniel S Greenwood, Jonathan A Ellman. Sulfur-Arylation of Sulfenamides via Ullmann-Type Coupling with (Hetero)aryl Iodides. Organic letters. 2023 Jun 30;25(25):4759-4764