An Interrupted Pummerer Reaction Mediated by a Hypervalent Iodine(III) Reagent: In Situ Formation of RSCl and Its Application for the Synthesis of 3-Sulfenylated Indoles
Beibei Zhang, Xuemin Li, Xiaoxian Li, Zhenyang Yu, Bingyue Zhao, Xiaofan Wang, Yunfei Du, Kang Zhao
Abstract
and sulfoxides was found to in situ generate reactive organosulfenyl chloride, which enabled the intramolecular electrophilic cyclization of 2-alkynylanilines, generating 3-sulfenylated indole with a good to excellent yield under metal-free conditions. One striking feature of the approach is that sulfoxide regeneration can be realized via the oxidation of the formed sulfides by the generated hypervalent iodine species.
Topics & Concepts
Hypervalent moleculeChemistryElectrophileReagentPummerer rearrangementSulfoxideIntramolecular forceIodineIndole testCombinatorial chemistryYield (engineering)In situSulfoneOrganic chemistryCatalysisMaterials scienceMetallurgyAcetic anhydrideSulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsOxidative Organic Chemistry Reactions