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Electrochemical Reductive Smiles Rearrangement for C-N Bond Formation
Xihao Chang1, Qinglin Zhang1, Chang Guo1
1Hefei National Laboratory for Physical Sciences at the Microscale , University of Science and Technology of China , Hefei 230026 , China.
Abstract:
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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