Sulfuryl Fluoride Mediated Synthesis of Amides and Amidines from Ketoximes via Beckmann Rearrangement
Jitendra Gurjar, Valery V. Fokin
Abstract
Abstract A metal‐free and redox‐neutral method for Beckmann rearrangement employing inexpensive and readily available SO 2 F 2 gas is described. The reported transformation proceeds at ambient temperature and is compatible with a wide range of sterically and electronically diverse aromatic, heteroaromatic, aliphatic and lignin‐like oximes providing amides in good to excellent yields. The reaction proceeds through the formation of an imidoyl fluoride intermediate that can also be used for the synthesis of amidines.
Topics & Concepts
Beckmann rearrangementChemistrySteric effectsFluorideOrganic chemistryCombinatorial chemistryOximeInorganic chemistryChemical Synthesis and AnalysisChemical Synthesis and ReactionsAsymmetric Hydrogenation and Catalysis