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One-Step Synthesis of Quinolines via Palladium-Catalyzed Cross-Coupling of Cyclopropanols with Unprotected ortho-Bromoanilines

Andrei Nikolaev, Nisha Nithiy, Arturo Orellana*

*Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada, Email: aorellanyorku.ca

A. Nikolaev, N. Nithiy, A. Orellana, Synlett, 2014, 25, 2301-2305.

DOI: 10.1055/s-0034-1378613 (free Supporting Information)


Abstract

A cross-coupling of unprotected ortho-bromoanilines with a wide range of cyclopropanols yields quinolines in a single operation via an intramolecular condensation and palladium-catalyzed oxidation sequence. Deuterium-labeling experiments provide direct evidence of a second equivalent of bromoaniline serving as the terminal oxidant.

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Key Words

cyclopropanols, cross-coupling, palladium, quinolines


ID: J60-Y2014