Synthesis of Isothiazoles and Isoselenazoles through Rhodium-Catalyzed Oxidative Annulation with Elemental Sulfur and Selenium
Sanghun Moon, Yuji Nishii, Masahiro Miura
Abstract
A rhodium-catalyzed oxidative annulation of benzimidates with elemental sulfur for the direct construction of isothiazole rings is reported. The proposed reaction mechanism involving Rh(I)/Rh(III) redox is supported by a stoichiometric reaction of metallacycle species as well as DFT calculations. This method is also applicable to selenium cyclization to produce isoselenazole derivatives. The alkoxy substituent at C3 can be used for further functionalization of the azole core.
Topics & Concepts
ChemistryAnnulationIsothiazoleRhodiumSeleniumCatalysisSulfurAlkoxy groupSubstituentStoichiometryOxidative additionCombinatorial chemistryOrganic chemistryMedicinal chemistryAlkylSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsOrganoselenium and organotellurium chemistry