PerspectiveCATALYSIS

The Mitsunobu reaction, reimagined

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Science  30 Aug 2019:
Vol. 365, Issue 6456, pp. 866-867
DOI: 10.1126/science.aay6635

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Summary

Nucleophilic substitution reactions are widely used to create carbon–heteroatom and carbon–carbon bonds as part of the synthesis of natural products and other organic molecules. These reactions typically involve a pronucleophile (NuH) and an electrophile that bears a suitable leaving group. Alcohols are often used as electrophiles because they are inexpensive and readily available. During the direct nucleophilic substitution between an alcohol and a pronucleophile, the alcohol's hydroxyl group would be replaced with the nucleophile, forming water as the sole byproduct. In the case of chiral secondary alcohols, the bimolecular substitution would lead to the substituted product with inverted stereochemistry. However, alcohols usually do not react with pronucleophiles without being activated prior to the substitution. On page 910 of this issue, Beddoe et al. (1) report an easily accessible catalyst that facilitates the direct nucleophilic substitution.

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