Sulfur-Arylation of Sulfenamides via Ullmann-Type Coupling with (Hetero)aryl Iodides
Nathaniel S. Greenwood, Jonathan A. Ellman
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.
Topics & Concepts
ArylChemistrySulfurSteric effectsIodideRing (chemistry)AlkylCatalysisCombinatorial chemistryCopperOrganic chemistrySulfur-Based Synthesis TechniquesSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods