Copper-Catalyzed Cyclization of 2-Alkynylanilines to Give 2-Haloalkoxy-3-alkyl(aryl)quinolines

Herein we describe a method to produce 2-haloalkoxy-3-substituted quinolines via the cyclization of 2-alkynylanilines with TMSCF3 and THF. This synthetic method uses inexpensive and easy-to-handle TMSCF3 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.

Automated summary

In this study, a method for producing 2-haloalkoxy-3-substituted quinolines via cyclization of 2-alkynylanilines with TMSCF3 and THF was described. This synthetic method utilizes inexpensive and easy-to-handle TMSCF3 and a commercially available CuI catalyst to efficiently transform a wide range of 2-alkynylanilines into versatile 2-difluoromethoxy-3-substituted quinolines and 2-iodoalkoxy-3-substituted quinolines with excellent chemoselectivity.