Copper-Catalyzed Cyclization of 2-Alkynylanilines to Give 2-Haloalkoxy-3-alkyl(aryl)quinolines
Dong Lu, Songhua Chen, Niu Tang, Shuang‐Feng Yin, Nobuaki Kambe, Renhua Qiu
Abstract
Herein we describe a method to produce 2-haloalkoxy-3-substituted quinolines via the cyclization of 2-alkynylanilines with TMSCF 3 and THF. This synthetic method uses inexpensive and easy-to-handle TMSCF 3 and employs a commercially available CuI catalyst to transform a broad range of 2-alkynylanilines into versatile 2-difluoromethoxy-3-substituted quinolines and 2-iodoalkoxy-3-substituted quinolines with excellent chemoselectivity.
Topics & Concepts
ChemoselectivityChemistryAlkylCatalysisArylCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCyclopropane Reaction Mechanisms