Transition-Metal-Free Selective Oxidative C(sp3)-S/Se Coupling of Oxindoles, Tetralone, and Arylacetamides: Synthesis of Unsymmetrical Organochalcogenides.

Transition-metal-free synthetic methods have been developed for the preparation of unsymmetrical diaryl and aryl alkyl chalcogenides: sulfones, sulfides, and selenides from the sp3-C-H bond of oxindole, tetralone, arylacetamide, and aryl chalcogenide precursors. Sulfones were obtained from sodium sulfinates using potassium iodide, tert-butyl hydroperoxide in DMSO, and acetic acid. Sulfides and selenides were prepared from diaryl disulfides or diselenides employing potassium tert-butoxide in DMSO. α-Tetralone underwent concomitant chalcogenation and aromatization resulting in 2-chalcogenyl-1-naphthols in one pot.