DOI: 10.1021/acs.orglett.6c04104 ISSN: 1523-7060
S -Arylsulfinamides via Photoredox-Catalyzed Arylation of N -Sulfinylamines with Diaryliodonium Salts
Polina V. Zaikina, Dmitry I. Bugaenko, Alexander V. KarchavaAbstract
A transition-metal-free, visible-light-mediated S-arylation of N-sulfinylamines using diaryliodonium salts and eosin Y efficiently affords diverse S-arylsulfinamides. This protocol tolerates both symmetrical diaryliodonium salts and unsymmetrical reagents bearing a 3,5-dimethylisoxazole (DMIX) auxiliary, enabling a highly chemoselective, one-pot C–H sulfinamidation of arenes. The utility of the method is demonstrated via the late-stage functionalization of drug-like molecules and downstream conversions of the resulting sulfinamides into diverse sulfur(VI) derivatives.