Synthesis of Carbamoyl Fluorides via a Selective Fluorinative Beckmann Fragmentation
Jin Song, Y. H. Shin
Abstract
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.
Topics & Concepts
Beckmann rearrangementChemistryFragmentation (computing)SelectivityCombinatorial chemistryStereochemistryOrganic chemistryCatalysisComputer scienceOperating systemFluorine in Organic ChemistrySynthesis and Reactions of Organic CompoundsSynthesis and Biological Evaluation