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Updated: Nov 16, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Cross-coupling reactions with esters, aldehydes, and alcohols
Yan-Long Zheng1, Stephen G Newman1
1Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada. stephen.newman@uottawa.ca.
New catalytic methods enable esters, aldehydes, and alcohols to participate in cross-coupling reactions, forming amides, ketones, and more. These advances offer efficient alternatives to traditional multi-step synthesis.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Cross-coupling reactions and π bond additions are fundamental in organic synthesis.
- Traditionally, these reaction classes employ distinct substrates and mechanisms.
- Recent advances reveal significant overlap, particularly using oxygenated organic compounds.
Purpose of the Study:
- To highlight recent catalytic transformations involving non-traditional carbon-based coupling partners.
- To emphasize the mechanistic insights enabling these reactions.
- To showcase efficient alternatives to conventional synthetic routes.
Main Methods:
- Nickel- and Palladium-catalyzed reactions.
- Utilizing esters, aldehydes, and alcohols as coupling partners.
- Mechanistic investigation of catalytic cycles.
Main Results:
- Successful formation of amides, ketones, substituted alcohols, and alkanes.
- Demonstration of esters, aldehydes, and alcohols as versatile coupling partners.
- Development of catalytic alternatives to stoichiometric methods.
Conclusions:
- Oxygenated organic compounds can be effectively incorporated into cross-coupling-like catalytic cycles.
- These methods provide streamlined and efficient synthetic strategies.
- Advances in catalysis bridge the gap between biaryl synthesis and π bond additions.
Related Concept Videos
Crossed Aldol Reactions: Overview
β-Dicarbonyl Compounds via Crossed Claisen Condensations
Crossed Aldol Reaction Using Weak Bases
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction
Esters to β-Ketoesters: Claisen Condensation Overview

