Synergistic Brønsted/Lewis acid catalyzed aromatic alkylation with unactivated tertiary alcohols or di- <i>tert</i> -butylperoxide to synthesize quaternary carbon centers
Aaron Pan, Maja Chojnacka, Robert Crowley, Lucas Göttemann, Brandon E. Haines, Kevin G. M. Kou
Abstract
-butylperoxide. This transformation inspired the development of a synergistic Brønsted/Lewis acid catalyzed aromatic alkylation that fills a gap in the Friedel-Crafts reaction literature by employing unactivated tertiary alcohols as alkylating agents, leading to new quaternary carbon centers. Corroborated by DFT calculations, the Lewis acid serves a role in enhancing the acidity of the Brønsted acid. The use of non-allylic, non-benzylic, and non-propargylic tertiary alcohols represents an underexplored area in Friedel-Crafts reactivity.
Topics & Concepts
AlkylationBrønsted–Lowry acid–base theoryCatalysisQuaternary carbonChemistryLewis acids and basesTertiary alcoholsCarbon fibersMedicinal chemistryOrganic chemistryEnantioselective synthesisMaterials scienceComposite materialComposite numberAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions