Synthesis of 2,3-Bis(trifluoromethylseleno) Indoles through an Oxidative Copper-Mediated Domino Reaction
Hui Wang, Yunfei Yao, Zipeng Zhang, Yangjie Huang, Zhiqiang Weng
Abstract
An oxidative copper-mediated double trifluoromethylselenolation of terminal 2-alkynylanilines using [(bpy)CuSeCF3]2 is reported, providing a moderately efficient and convenient approach to 2,3-bis(trifluoromethylseleno)indoles. Mechanistic studies show that a cascade sequence of oxidation, trifluoromethylselenolation, 5-endo-dig cyclization, and elimination is involved in this transformation.
Topics & Concepts
ChemistryDominoOxidative phosphorylationCascade reactionCopperCombinatorial chemistrySequence (biology)Transformation (genetics)CascadeStereochemistryOrganic chemistryCatalysisBiochemistryGeneChromatographyFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods