Related Experiment Video
Updated: Sep 18, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Cu-Catalyzed Acylation of Quinoline-N-oxides with gem-Difluorostyrenes via the Tandem
Yang Feng1, Yuanyuan Wu1, Zengjiang Yue1
1Key Laboratory of Eco-Functional Polymer Materials of the Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. China.
Abstract:
The copper-catalyzed defluorination and decarbonization cross-coupling reaction between quinoline-N-oxides and gem-difluorostyrenes via key 2-arylmethylquinoline intermediates to access 2-aroylquinolines is described. Versatile 2-aroylquinolines were obtained in up to 83% yield with exclusive regioselectivity. The detailed reaction mechanism investigation shows that it undergoes a tandem [3 + 2] cycloaddition/elimination of formyl difluoride/oxidation of 2-arylmethylquinolines. This copper-catalyzed transformation proceeds efficiently at 90 °C, eliminating the necessity for exogenous oxidants or hazardous reagents, while maintaining excellent functional group tolerance.
Related Concept Videos
Cycloaddition Reactions: Overview
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Nucleophilic Aromatic Substitution: Elimination–Addition
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Cycloaddition Reactions: MO Requirements for Thermal Activation

