TfOH-Catalyzed Regioselective S–H Insertion of Cyclic Thioamide Derivatives with Diazo Compounds at Room Temperature
Chunyan Li, Rui Wang, Huang Li, Jiale Chen, Jingru Jin, Qiongjiao Yan, Wei Wang, Haifeng Wang, Fen‐Er Chen
Abstract
We have developed a method for highly regioselective S-H bond insertion reactions of various diazo compounds and cyclic thioamide derivatives at room temperature. These reactions provide straightforward access to alkylated benzimidazoles, benzothiazoles, and benzoxazoles. This mild method uses readily available TfOH as a catalyst and features a broad substrate scope, good functional group tolerance, good to excellent yields, and high regioselectivities.
Topics & Concepts
ThioamideChemistryRegioselectivityDiazoCatalysisFunctional groupAlkylationCombinatorial chemistrySubstrate (aquarium)Organic chemistryGeologyOceanographyPolymerCyclopropane Reaction MechanismsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods