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Synthesis of Carbamoyl Fluorides via a Selective Fluorinative Beckmann Fragmentation

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journal contribution
posted on 01.07.2021, 18:03 by Jin Woo Song, Hee Nam Lim
A fluorinative Beckmann fragmentation of α-oximinoamides was devised to provide synthetically useful carbamoyl fluorides. High selectivity for fragmentation over a potentially competing Beckmann rearrangement was observed. This protocol has a distinct mechanism and thus a different substrate scope compared with other synthetic methods. α-Oximinoamides derived from the readily available secondary amines, lactams, or isatins were converted into structurally diverse carbamoyl fluorides.