Direct Assembly of Phthalides via Calcium(II)-Catalyzed Cascade <i>ortho</i>-C-Alkenylation/Hydroacyloxylation of 3-Aminobenzoic Acids with Alkynes in Hexafluoroisopropanol
Qingmei Liu, Zhi Zhou, Minyao Kuang, Hui Gao, Wei Yi, Shengdong Wang
Abstract
By virtue of a calcium(II)/hexafluoroisopropanol cocatalytic system, the efficient and practical coupling of 3-aminobenzoic acids with alkynes has been realized, giving direct and regioselective access to the phthalide framework with good substrate/functional group compatibility. Mechanistic studies identified 3-amino-2-vinylbenzoic acid species as the active intermediate, thereby revealing an ortho-C-alkenylation/hydroacyloxylation cascade for this transformation.
Topics & Concepts
ChemistryPhthalideRegioselectivityCatalysisCascadeCalciumCombinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryChromatographyCatalytic C–H Functionalization MethodsChemical Synthesis and ReactionsOxidative Organic Chemistry Reactions