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SYNTHETIC METHODOLOGY

Fragmentation and reassembly

Nature Chemistry volume 13, pages 110–111 (2021)Cite this article

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Metal-catalysed hydroformylations efficiently convert feedstock alkenes into aldehydes, though typically relatively simple ones. Now, the palladium-catalysed fragmentation of acid chlorides followed by reassembly with alkynes and silanes has been shown to form valuable, highly substituted α,β-unsaturated aldehydes.

The generation and manipulation of carbonyl functionalities is one of the most common reactions performed in organic synthesis. While a diverse array of reactions are available to access carbonyl products, some of the most efficient are metal-catalysed carbonylations1. This is illustrated by the scale of aldehyde synthesis using metal-catalysed hydroformylation reactions — the addition of hydrogen and carbon monoxide to an alkene — reaching over 10 million tons per year2. The usefulness of this transformation has inspired continued interest in designing more active and more selective catalysts, as well as broadening its scope of application.

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Fig. 1: A versatile, palladium-catalysed carboformylation reaction to prepare highly substituted α,β-unsaturated aldehydes.

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  1. Department of Chemistry, McGill University, Montreal, Quebec, Canada

    José Zgheib & Bruce A. Arndtsen

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  1. José Zgheib
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  2. Bruce A. Arndtsen
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Correspondence to Bruce A. Arndtsen.

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Zgheib, J., Arndtsen, B.A. Fragmentation and reassembly. Nat. Chem. 13, 110–111 (2021). https://doi.org/10.1038/s41557-020-00631-9

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