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Updated: Apr 12, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Selective Pinacol Coupling on Regeneratable Supported Acids in Sole Water
Nicolas Sotto1, Muriel Billamboz1, Carole Chevrin-Villette1
1†Sorbonne Universités, Université de Technologie de Compiègne, Ecole Supérieure de Chimie Organique et Minérale, EA 4297 Transformations Intégrées de la Matière Renouvelable, Centre de Recherche Royallieu, CS 60 319, F-60203 Compiègnecedex, France.
This study presents an efficient pinacol coupling reaction using water as a solvent, a reusable supported acid catalyst, and zinc. The method offers enhanced selectivity and catalyst recyclability for sustainable chemical synthesis.
Area of Science:
- Organic Chemistry
- Green Chemistry
- Catalysis
Background:
- Pinacol coupling is a vital carbon-carbon bond-forming reaction.
- Traditional methods often employ harsh conditions or non-recyclable catalysts.
- Developing sustainable and efficient synthetic routes is crucial in modern chemistry.
Purpose of the Study:
- To develop an efficient and environmentally friendly pinacol coupling reaction.
- To utilize a reusable heterogeneous catalyst for improved sustainability.
- To enhance reaction selectivity using supported acid catalysts.
Main Methods:
- Pinacol coupling reaction performed in water as the sole solvent.
- Utilized a reusable heterogeneous supported acid as the catalyst.
- Employed zinc as a cost-effective metal source.
- Investigated catalyst regeneration and reusability up to 10 cycles.
Main Results:
- Achieved efficient pinacol coupling in aqueous medium.
- Demonstrated high reusability of the supported acid catalyst (10-fold regeneration without activity loss).
- Observed enhanced selectivity compared to homogeneous acid catalysts.
- Confirmed zinc as a suitable and economical metal source.
Conclusions:
- The developed method provides a sustainable and efficient approach to pinacol coupling.
- Heterogeneous supported acids offer advantages in selectivity and recyclability for this transformation.
- Water as a solvent and reusable catalysts contribute to greener chemical processes.
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