Synthesis of Benzo[<i>b</i>]thiophenes through Rhodium‐Catalyzed Three‐Component Reaction using Elemental Sulfur
Sanghun Moon, Moena Kato, Yuji Nishii, Masahiro Miura
Abstract
Abstract A benzo[ b ]thiophene synthesis by Rh‐catalyzed three‐component coupling reaction of arylboronic acids, alkynes, and elemental sulfur (S 8 ) is developed. A notable feature of this protocol is that the thienannulation (thiophene annulation) proceeds with high regioselectivity via the sequential alkyne insertion, C−H activation, and then sulfur atom transfer to the metallacycle intermediate. In a similar manner, dibenzothiophenes can be synthesized from the parent biarylboronic acids and S 8 . magnified image
Topics & Concepts
ChemistryRegioselectivitySulfurThiopheneRhodiumCatalysisAnnulationAlkyneMetallacycleCoupling reactionMedicinal chemistryOrganic chemistryStereochemistryX-ray crystallographyPhysicsDiffractionOpticsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions