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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

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Selective Pinacol-Coupling Reaction using a Continuous Flow System.

Nicolas Sotto¹, Clément Cazorla¹, Carole Villette²

¹Sorbonne Universités, Université de Technologie de Compiègne , Centre de Recherche Royallieu, CS 60 319, F-60203 Compiègne cedex, France.

The Journal of Organic Chemistry

|November 3, 2016

Summary

This summary is machine-generated.

A novel continuous flow pinacol coupling reaction using zinc(0) was developed, achieving high yields in just 2 minutes. This efficient flow method surpasses traditional batch processes for producing valuable carbonyl compounds.

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Area of Science:

Organic Chemistry
Green Chemistry
Process Chemistry

Background:

Pinacol coupling is a vital reaction for creating valuable organic compounds.
Traditional batch methods for pinacol coupling can be time-consuming and less efficient.
Developing continuous flow processes offers potential for improved reaction control and productivity.

Purpose of the Study:

To develop the first continuous flow pinacol coupling reaction for carbonyl compounds.
To optimize reaction conditions for high yield and productivity.
To compare the efficiency of the flow method against traditional batch processes.

Main Methods:

Utilized a continuous flow cartridge packed with zinc(0) for the reaction.
Optimized reaction time to achieve completion within a single pass (2 minutes).
Investigated the scope and limitations of the methodology with various carbonyl compounds.

Main Results:

Successfully achieved continuous flow pinacol coupling in only 2 minutes.
Demonstrated efficient gram-scale production of value-added compounds with high productivity.
Showed high efficiency for aromatic and α,β-unsaturated aldehydes, with moderate results for acetophenone derivatives.
The flow method yielded superior results in terms of yield and selectivity compared to batch methods.

Conclusions:

The developed continuous flow method represents a significant advancement in pinacol coupling reactions.
This methodology offers a faster, more productive, and selective alternative to batch processing.
The flow system is particularly effective for certain classes of carbonyl compounds, paving the way for streamlined synthesis.