Photocatalytic C–C Bond Cleavage and Fluorosulfonylation of Strained Cycloalkanols for Carbonyl-Containing Aliphatic Sulfonyl Fluorides
Zhi-Min Yan, Qi Lin, Huijie Du, Ziqiang Zhao, Jiali Liu, Yichen Dong, Wei Li, Lijin Wang
Abstract
In this report, we present a photocatalytic ring-opening fluorosulfonylation of strained cycloalkanols with sulfur dioxide and NFSI under mild conditions for the synthesis of carbonyl-containing aliphatic sulfonyl fluorides. The synthetic potential of the carbonyl-containing aliphatic sulfonyl fluoride products has been examined by diverse transformations, including SuFEx reactions and Baeyer–Villiger oxidation reactions. Mechanistic studies demonstrate that the reaction operates through a radical C–C bond cleavage/SO 2 insertion/fluorination cascade process.
Topics & Concepts
ChemistrySulfonylBond cleavagePhotocatalysisCleavage (geology)FluorideRing (chemistry)SulfurPhotochemistryMedicinal chemistryCatalysisOrganic chemistryInorganic chemistryFracture (geology)EngineeringAlkylGeotechnical engineeringSulfur-Based Synthesis TechniquesFluorine in Organic ChemistryRadical Photochemical Reactions