Visible-light photoredox-catalyzed dual C–C bond cleavage: synthesis of 2-cyanoalkylsulfonylated 3,4-dihydronaphthalenes through the insertion of sulfur dioxide
Yu Liu, Qiaolin Wang, Zan Chen, Hua Li, Biquan Xiong, Panliang Zhang, Kewen Tang
Abstract
An efficient novel visible-light photoredox-catalyzed dual carbon-carbon bond cleavage of methylenecyclopropanes and cycloketone oximes for the synthesis of 2-cyanoalkylsulfonated 3,4-dihydronaphthalenes through the insertion of sulfur dioxide is established. This dual cleavage of carbon-carbon bonds involves a radical pathway and goes through a sequence of iminyl radical formation, carbon-carbon bond cleavage, sulfur dioxide insertion, sulfonyl radical addition, another carbon-carbon bond cleavage, and intramolecular cyclization.
Topics & Concepts
ChemistryIntramolecular forceSulfurCleavage (geology)PhotochemistryBond cleavageCatalysisCarbon fibersVisible spectrumOrganic chemistryMaterials scienceOptoelectronicsComposite materialComposite numberFracture (geology)Sulfur-Based Synthesis TechniquesRadical Photochemical ReactionsChemical Synthesis and Reactions