Catalytic Chemoselective Sulfimidation with an Electrophilic [Co^III (TAML)]^- -Nitrene Radical Complex*.

ABSTRACT: The cobalt species PPh₄ [Co^III (TAML^red )] is a competent and stable catalyst for the sulfimidation of (aryl)(alkyl)-substituted sulfides with iminoiodinanes, reaching turnover numbers up to 900 and turnover frequencies of 640 min^-1 under mild and aerobic conditions. The sulfimidation proceeds in a highly chemoselective manner, even in the presence of alkenes or weak C-H bonds, as supported by inter- and intramolecular competition experiments. Functionalization of the sulfide substituent with various electron-donating and electron-withdrawing arenes and several alkyl, benzyl and vinyl fragments is tolerated, with up to quantitative product yields. Sulfimidation of phenyl allyl sulfide led to [2,3]-sigmatropic rearrangement of the initially formed

SUBMITTER: van Leest NP 

PROVIDER: S-EPMC7839782 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature