CuBr<sub>2</sub>-Catalyzed Annulation of 2-Bromo-<i>N</i>-Arylbenzimidamide with Se/S<sub>8</sub> Powder for the Synthesis of Benzo[<i>d</i>]isoselenazole and Benzo[<i>d</i>]isothiazole
Quanyuan Wang, Fuhong Xiao, Zhi Huang, Guojiang Mao, Guo‐Jun Deng
Abstract
A CuBr 2 -catalyzed annulation of 2-bromo- N -arylbenzimidamide with selenium/sulfur powder for the synthesis of benzo[ d ]isoselenazole and benzo[ d ]isothiazole in generally good yields was investigated. This synthetic strategy features good substrate scope and functional group tolerance. Furthermore, the corresponding products could be converted into N -aryl indoles via rhodium III -catalyzed ortho C–H activation of the N -phenyl ring, providing an efficient approach for axial aromatic molecules.
Topics & Concepts
AnnulationIsothiazoleChemistryCatalysisArylSubstrate (aquarium)MoleculeRing (chemistry)StereochemistrySeleniumMedicinal chemistryOrganic chemistryAlkylOceanographyGeologySulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsOrganoselenium and organotellurium chemistry