Phototropin-Inspired Chemoselective Synthesis of Unsymmetrical Disulfides: Aerobic Oxidative Heterocoupling of Thiols Using Flavin Photocatalysis
Marina Oka, Daichi Katsube, Takeshi Tsuji, Hiroki Iida
Abstract
Inspired by the photochemical mechanism of a plant blue-light receptor, a unique flavin-based photocatalytic system was developed for the chemoselective heterocoupling of two different thiols, which enabled the facile synthesis of unsymmetrical disulfides. Owing to the redox- and photo-organocatalysis of flavin, the coupling reaction took place under mild metal-free conditions and visible light irradiation with the use of air, which is recognized as the ideal green oxidant.
Topics & Concepts
Flavin groupChemistryPhotocatalysisPhototropinPhotochemistryRedoxOxidative phosphorylationCombinatorial chemistryOxidative coupling of methaneVisible spectrumCatalysisOrganic chemistryCryptochromeBiochemistryEnzymeCircadian clockGeneOptoelectronicsPhysicsSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsPhotochromic and Fluorescence Chemistry