Photocatalyzed Decarboxylative Thiolation of Carboxylic Acids Enabled by Fluorinated Disulfide
Mikhail O. Zubkov, Mikhail D. Kosobokov, Vitalij V. Levin, Alexander D. Dilman
Abstract
Thiolation of carboxylic acids using a disulfide reagent having tetrafluoropyridinyl groups is described. The light-mediated process is performed using an acridine-type photocatalyst. Primary, secondary, tertiary, and heteroatom-substituted carboxylic acids can be thiolated, and the method can be applied to the late-stage modification of a range of naturally occurring compounds and drugs. The fluorinated pyridine fragment is believed to enable the C-S bond formation. The resulting sulfides were used as redox-active radical precursors.
Topics & Concepts
ChemistryReagentDisulfide bondHeteroatomPrimary (astronomy)PyridineCarboxylic acidCombinatorial chemistryPhotocatalysisOrganic chemistryCatalysisRing (chemistry)BiochemistryPhysicsAstronomySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsChemical Synthesis and Reactions