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Updated: Jul 5, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Cross-Coupling of Benzylic and Aldehydic C-H Bonds via Photocatalytic Tandem Radical-Radical Coupling and
Yunfei Guo1, Jipeng Qi1, Hongyu Guo1
1College of Chemistry, Taiyuan University of Technology, Taiyuan, Shanxi 030024, P. R. China.
Abstract:
The construction of a C-C bond by cross-coupling of two different C-H bonds with the release of hydrogen gas represents an ideal yet challenging bond formation strategy. Herein, we report a photocatalytic metal-free cross-coupling of benzylic and aldehydic C-H bonds by synergistic catalysis of organophotocatalyst 4CzIPN and a thiol, which affords the corresponding α-aryl ketones in acceptable yields along with hydrogen evolution. The mechanistic investigation indicates a radical-radical coupling to give an intermediary alcohol, followed by an acceptorless alcohol dehydrogenation.
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