Gold-Catalyzed Formal Hexadehydro-Diels–Alder/Carboalkoxylation Reaction Cascades
Hongfa Wang, Linna Guo, Zhi-Bo Fan, Tianhua Tang, Weiwei Zi
Abstract
A dual gold-catalyzed hexadehydro-Diels-Alder/carboalkoxylation cascade reaction is reported. In this transformation, the gold catalyst participated in the hexadehydro-Diels-Alder step, switching the mechanism from a radical type to a cationic one, and then the catalyst activated the resulting aryne to form an ortho-Au phenyl cation species, which underwent a carboalkoxylation rearrangement rather than the expected aryne-ene reaction.
Topics & Concepts
AryneChemistryCatalysisCationic polymerizationDiels–Alder reactionCascadeCascade reactionMedicinal chemistryCombinatorial chemistryOrganic chemistryChromatographyCyclization and Aryne ChemistryCatalytic Alkyne ReactionsChemical synthesis and alkaloids