Assembly of Thiosubstituted Benzoxazoles via Copper-Catalyzed Coupling of Thiols with 5-Iodotriazoles Serving as Diazo Surrogates
Yury N. Kotovshchikov, Gennadij V. Latyshev, Е. А. Кириллова, Uliana D. Moskalenko, Nikolay V. Lukashev, I. P. Beletskaya
Abstract
An efficient cascade approach to thiosubstituted benzoxazoles has been developed. The transformation starts with in situ generation of a diazo compound via annulation-triggered electrocyclic opening of the 1,2,3-triazole ring. The subsequent Cu-catalyzed trapping of diazo intermediates by various thiols affords the desired heterocycles in generally good yields of up to 91%. The protocol features very good functional group tolerance and is applicable to substrates with different electronic properties.
Topics & Concepts
DiazoChemistryAnnulationCombinatorial chemistryFunctional groupCatalysisCopperRing (chemistry)CascadeStereochemistryMedicinal chemistryOrganic chemistryPolymerChromatographyCyclopropane Reaction MechanismsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods