Sulfuryl Fluoride Mediated Synthesis of Amides and Amidines from Ketoximes via Beckmann Rearrangement |
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Authors: | Jitendra Gurjar Prof Dr Valery V Fokin |
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Institution: | University of Southern California, The Bridge@USC and Loker Hydrocarbon Research Institute, 1002 Childs Way, Los Angeles, CA, 90089-3502 USA |
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Abstract: | A metal-free and redox-neutral method for Beckmann rearrangement employing inexpensive and readily available SO2F2 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. |
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Keywords: | amidines Beckmann rearrangement lignin sulfuryl fluoride synthetic methods |
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