Merging Hydrogen Atom Transfer and Halogen Atom Transfer for Iodide-Catalyzed Radical Reductive Cyclization of 1,6-Enynes
Linglong Ding, Yi-Hui Deng, Tian‐Yu Sun, Yuqin Jiang, Xiao‐Feng Xia
Abstract
Described herein is the development of a metal-free iodide-catalyzed radical reductive cyclization of 1,6-enynes. A strategy involving in situ iodination/radical cyclization/silyl radical-mediated halogen atom transfer/hydrogen atom transfer for the synthesis of functionalized pyrrolidines has been proposed. Using this halogen-atom abstraction protocol, 1,6-enynes with various vinyl halides including inert fluorides, chlorides, and reactive bromides could be transformed into substituted pyrroles via a multistep radical isomerization process.
Topics & Concepts
ChemistryHalogenIodideHydrogen atomHydrogen atom abstractionCatalysisHalogenationHalideRadical cyclizationIsomerizationSilylationPhotochemistryRadical initiatorAtom (system on chip)Reductive eliminationMedicinal chemistryRadicalOrganic chemistryAlkylPolymerizationComputer scienceEmbedded systemPolymerRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry