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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Chemical Consequences of the Mechanical Bond: A Tandem Active Template-Rearrangement Reaction
Florian Modicom1, Ellen M G Jamieson1, Elise Rochette1
1Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, UK.
Abstract:
We report the unexpected discovery of a tandem active template CuAAC-rearrangement process, in which N2 is extruded on the way to the 1,2,3-triazole product to give instead acrylamide rotaxanes. Mechanistic investigations suggest this process is dictated by the mechanical bond, which stabilizes the CuI -triazolide intermediate of the CuAAC reaction and diverts it down the rearrangement pathway; when no mechanical bond is formed, the CuAAC product is isolated.
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