Benzothiazole Synthesis: Mechanistic Investigation of an In Situ-Generated Photosensitizing Disulfide
Ho Seong Hwang, Sumin Lee, Sung Su Han, Yu Kyung Moon, Youngmin You, Eun Jin Cho
Abstract
The use of a visible light absorbing intermediate as a photosensitizer makes a chemical process simple and sustainable, obviating the need for the use of chemical additives. Herein, the formation of a photosensitizing disulfide in benzothiazole synthesis from 2-aminothiophenol and aldehydes was proposed and confirmed through in-depth mechanistic studies. A series of photophysical and electrochemical investigations revealed that an in situ-generated disulfide photosensitizes molecular oxygen to generate the key oxidants, singlet oxygen and superoxide anion, for the dehydrogenation step.
Topics & Concepts
BenzothiazoleChemistrySinglet oxygenPhotosensitizerDehydrogenationPhotochemistryChemical synthesisElectrochemistrySuperoxideDisulfide bondCombinatorial chemistryIn situOrganic chemistryOxygenCatalysisIn vitroBiochemistryElectrodePhysical chemistryEnzymeSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsOxidative Organic Chemistry Reactions