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Updated: Dec 26, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Iridium-Catalyzed Selective Cross-Coupling of Ethylene Glycol and Methanol to Lactic Acid
Jiajie Wu1, Lingyun Shen1, Zhe-Ning Chen2
1Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai, 200438, P. R. China.
Abstract:
An atom-economic approach that has an unprecedented high selectivity for the synthesis of lactic acid (LA) based on a catalytic dehydrogenative cross-coupling by using inexpensive bulk ethylene glycol and methanol is described. This method relies on the synthesis and utilization of a novel iridium catalyst bearing three N-heterocyclic carbenes derived from 1,3-dimethylbenzimidazolium salts, and exhibits outstanding activity in the production of LA [turnover frequency (TOF) up to 3660 h-1 ] owing to an elegant metal-ligand cooperation.
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