Formation of Cyclic Sulfinates and Sulfinamides through Homolytic Substitution at the Sulfur Atom

Abstract

Ring road: Cyclic sulfinates and sulfinamides can be synthesized by homolytic substitution to give alkyl and benzofused families of compounds. The presence of an additional heteroatom in the ring allows the preparation of sulfur-based heterocycles that are useful synthetic intermediates (see scheme). The stereogenic sulfur atom transfers its chirality to prochiral radicals. TTMSS=tris(trimethylsilyl)silane, AIBN=azobisisobutyronitrile.