Affiliation:
1. Key Laboratory of Functional Molecular Solids Ministry of Education Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base) College of Chemistry and Materials Science Anhui Normal University Wuhu 241000 P. R. China
2. Roy and Diana Vagelos Laboratories Department of Chemistry University of Pennsylvania 231 South 34th Street Philadelphia PA 19104–6323 USA
Abstract
AbstractA mild photoredox catalyzed construction of sulfides, disulfides, selenides, sulfoxides and sulfones from unstrained ketone precursors is introduced. Combination of this deacylative process with SN2 or coupling reactions provides novel and convenient modular strategies toward unsymmetrical or symmetric disulfides. Reactivity studies favor a bromine radical that initiates a HAT (Hydrogen Atom Transfer) from the aminal intermediate resulting in expulsion of a C‐centered radical that is intercepted to make C−S and C−Se bonds. Gram scale reactions, broad substrate scope and tolerance towards various functional groups render this method appealing for future applications in the synthesis of organosulfur and selenium complexes.
Funder
Division of Chemistry
National Natural Science Foundation of China
Natural Science Foundation of Anhui Province
Subject
General Chemistry,Catalysis