Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 46, Pages 10402-10405Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201905358
Keywords
amidines; Beckmann rearrangement; lignin; sulfuryl fluoride; synthetic methods
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Funding
- National Science Foundation [CHE-1660373]
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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.
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