Synthesis of Carbamoyl Fluorides Using a Difluorophosgene Surrogate Derived from Difluorocarbene and Pyridine N-Oxides

Dusty Cadwallader, Tristan R. Tiburcio, George A. Cieszynski and Christine M. Le*

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

D. Cadwaller, T. R. Tiburcio, G. A. Cieszynski, C. M. Le, J. Org. Chem., 2022, 87, 11457-11468.

DOI: 10.1021/acs.joc.2c01017

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Abstract

The combination of readily accessible starting materials provide a surrogate for toxic difluorophosgene (COF₂) gas that enables a synthesis of carbamoyl fluorides. This protocol does not require the use of pre-functionalized substrates, the preparation of light-, temperature-, and/or moisture-sensitive chemicals, or the application of explosive fluorinating reagents.

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proposed mechanisms

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Key Words

carbamoylation, fluorination, difluorocarbene, pyridine N-oxides

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ID: J42-Y2022