Journal
ORGANIC LETTERS
Volume 21, Issue 1, Pages 10-13Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03178
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Funding
- National Natural Science Foundation of China [21702198]
- Anhui Provincial Natural Science Foundation [1808085MB30]
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A conceptually new and synthetically valuable radical Smiles rearrangement reaction is reported under undivided electrolytic conditions. This protocol employs an entirely new strategy for the electrochemical radical Smiles rearrangement. Remarkably, an amidyl radical generated from the cleavage of the N-O bond under reductive electrolytic conditions plays a crucial role in this transformation. Various hydroxylamine derivatives bearing different substituents are suitable in this electrochemical transformation, furnishing the corresponding amides in up to 86% yield.
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