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Updated: Jun 24, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Photocatalyzed Cascade Hydrogen Atom Transfers for Assembly of Multi-Substituted α-SCF3 and α-SCF2H Cyclopentanones
Nicolas Marie1, Jun-An Ma2, Vincent Tognetti1
1CNRS, UMR 6014 COBRA, Univ Rouen Normandie, INSA Rouen Normandie, Normandie Univ, INC3M FR 3038, F-76000, Rouen, France.
Abstract:
A photocatalyzed formal (3+2) cycloaddition has been developed to construct original polysubstituted α-SCF3 cyclopentanones in a regio- and diastereoselective manner. This building block approach leverages trifluoromethylthio alkynes and branched/linear aldehydes, as readily available reaction partners, in consecutive hydrogen atom transfers and C-C bond formations. Difluoromethylthio alkynes are also compatible substrates. Furthermore, the potential for telescoped reaction starting from alcohols instead of aldehydes was demonstrated, as well as process automatization and scale-up under continuous microflow conditions. This prompted density functional theory (DFT) calculations to support a radical-mediated cascade process.
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