Catalytic Friedel–Crafts Alkylation of Electron Rich Aromatic Derivatives with α-Aryl Diazoacetates Mediated by Brønsted Acids
Rafael D. C. Gallo, Patrícia B. Momo, David P. Day, Antonio C. B. Burtoloso
Abstract
The catalytic protonation of aryl diazoacetates by strong Brønsted acids, followed by a Friedel-Crafts alkylation reaction with electron rich aromatic compounds, is reported. The reaction provided in a direct fashion 24 geminal diarylacetates in yields of ≤92%.
Topics & Concepts
Friedel–Crafts reactionChemistryProtonationGeminalArylAlkylationCatalysisBrønsted–Lowry acid–base theoryAromaticityOrganic chemistryMedicinal chemistryMoleculeIonAlkylCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions