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

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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… Click to show full abstract

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.

Keywords: catalyzed cyclization; alkynylanilines give; cyclization; cyclization alkynylanilines; substituted quinolines; copper catalyzed

Journal Title: Organic letters
Year Published: 2023

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