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BF3-Catalyzed Intramolecular Fluorocarbamoylation of Alkynes via Halide Recycling

E. Ali McKnight, Ramon Arora, Ekadashi Pradhan, Yuriko H. Fujisato, Ayonitemi J. Ajayi, Mark Lautens, Tao Zeng* and Christine M. Le*

*Department of Chemistry, York University, Toronto, Ontario M3J 1P3, Canada, Email: tzengyorku.ca, cmleyorku.ca

E. A. McKnight, R. Arora, E. Pradhan, Y. H. Fujisato, A. J. Ajayi, M. Lautens, T. Zeng, C. M. Le, J. Am. Chem. Soc., 2023, 145, 11012-11018.

DOI: 10.1021/jacs.3c03982


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Abstract

A BF3-catalyzed atom-economical fluorocarbamoylation reaction of alkyne-tethered carbamoyl fluorides provides 3-(fluoromethylene) oxindoles and γ-lactams with excellent stereoselectivity. The catalyst acts as both a fluoride source and Lewis acid activator, thereby enabling the formal insertion of alkynes into strong C-F bonds through a halide recycling mechanism.

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Key Words

Oxindoles


ID: J48-Y2023