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Mitsunobu gets a makeover

Nature Chemistry volume 11, pages 966–967 (2019)Cite this article

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Nucleophiles directly substitute alcohols in the Mitsunobu reaction, but the process uses hazardous materials and generates an excessive amount of toxic waste. More than 50 years on from its initial discovery, chemists report a new catalytic version of the reaction, with water as the only by-product.

Marmite is a yeast extract foodstuff that is famed in the British Isles under the slogan “you either love it or you hate it”. People love Marmite because of its strong savoury flavour and bitter aftertaste, and yet other people hate Marmite because of its strong savoury flavour and bitter aftertaste. A chemical reaction equivalent of Marmite is the Mitsunobu reaction; a powerful transformation where alcohols function as electrophilic coupling partners with nucleophiles1. Chemists love the Mitsunobu reaction as ubiquitous alcohols are used directly without recourse to form a more reactive functional group, such as a halide or sulfonate ester; and chemists hate Mitsunobu reactions because of the hazardous reagents, stoichiometric waste products, and complicated purifications. Writing in Science, Ross Denton and collaborators from GlaxoSmithKline have produced a remarkable feat of catalyst engineering that removes the need for stoichiometric reagents in the Mitsunobu reaction, and produces water as the only by-product2.

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Fig. 1: The classic Mitsunobu reaction and the development of a catalytic variant.

References

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  1. twitter: @AndyMcNally367

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  1. Department of Chemistry, Colorado State University, Fort Collins, CO, United States

    Andy McNally

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  1. Andy McNally
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Correspondence to Andy McNally.

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McNally, A. Mitsunobu gets a makeover. Nat. Chem. 11, 966–967 (2019). https://doi.org/10.1038/s41557-019-0362-2

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  • DOI: https://doi.org/10.1038/s41557-019-0362-2

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