AI Article Synopsis
- The Staudinger reaction is a technique that safely reduces unstable azides into amines, enabling the synthesis of important compounds in pharmaceuticals and natural products.
- It involves a nucleophilic attack by a trivalent phosphine, forming a reactive triazenide intermediate.
- Recent research demonstrates how a divalent phosphorus biradicaloid can react with azides, allowing for the capturing and characterization of the intermediate through experimental data and quantum chemical calculations.
Article Abstract
The Staudinger reaction provides chemists with a valuable tool for the reduction of azides, which are notoriously unstable and can decompose explosively. By providing a controlled method for the conversion of azides to amines, the reaction opened up new avenues for the synthesis of various amine-containing compounds that are widely used in natural products, pharmaceuticals and polymers. The Staudinger reaction begins with the nucleophilic attack of a trivalent phosphine (usually triphenylphosphine), leading to the formation of a triazenide intermediate, a highly reactive species. Here we report how a divalent phosphorus-centered biradicaloid reacts with covalent azides and show that it is possible to capture and fully characterize the transient intermediate. The experimental data is supported by quantum chemical calculations of the reaction paths and in terms of thermodynamics and chemical bonding.
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| http://dx.doi.org/10.1002/chem.202403893 | DOI Listing |
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