Visible‐Light‐Driven Remote C−H Chlorination of Aliphatic Sulfonamides with Sodium Hypochlorite
Yan‐Shuo Zhu, Juanjuan Wang, Danhua Wu, Wei Yu
Abstract
Abstract The C(sp 3 )−H chlorination of aliphatic sulfonamides was realized by visible‐light photoredox catalysis with Ru(bpy) 3 Cl 2 as photocatalsyt and NaOCl⋅5H 2 O crystals as the chlorinating agent. The reaction proceeds in a tandem pattern of N−H chlorination and Hofmann‐Löffler‐Freytag chlorination. A variety of differently substituted sulfonamides were chlorinated in this way in high yield. A radical‐chain mechanism is proposed for the reaction on the basis of experimental evidence.
Topics & Concepts
ChemistrySodium hypochloriteVisible spectrumYield (engineering)HypochloriteCatalysisPhotochemistryTandemOrganic chemistryMedicinal chemistryMetallurgyMaterials scienceOptoelectronicsPhysicsComposite materialCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsOxidative Organic Chemistry Reactions