Cascade Radical Annulation of 2-Alkynylthio(seleno)anisoles with Acetone or Acetonitrile: Synthesis of 3-Acetomethyl- or Cyanomethyl-Substituted Benzothio(seleno)phenes
Dichapong Kanjanawasee, Fangqi Shen, Yuqi Ni, Huiting Xu, Runpu Shen, Yuzhen Gao
Abstract
An efficient method for the direct preparation of 3-aceto(cyano)methyl-substituted benzothio(seleno)phenes has been achieved through C(sp3)–H bond activation of easily available acetone or acetonitrile and cascade radical cyclization reaction. In this cascade radical cyclization reaction, C(sp2)–C(sp3) and C(sp2)–S bonds, as well as benzenethio(seleno)phene skeletons, can be built along with the cleavage of the C(sp3)–S bond, demonstrating the high step-economics and efficiency of this approach.
Topics & Concepts
ChemistryAnnulationAcetonitrileAcetoneCascadeBond cleavageTriple bondCascade reactionRadical cyclizationCleavage (geology)Medicinal chemistryKetoneOne-StepPhotochemistryOrganic chemistryDouble bondCatalysisFracture (geology)ChromatographyGeotechnical engineeringArtEngineeringVisual artsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions