Vicinal diamines are structural motifs frequently found in pharmaceuticals – with penicillin, Tamiflu and many anti-cancer agents being prominent examples. Their wide use has motivated researchers to develop an efficient way to prepare the motifs, but so far this has proved tricky.
“Elegant methods have been developed for making vicinal diamines of specific structures, but a unified approach to their synthesis remains elusive,” says Song Lin, researcher at the Department of Chemistry and Chemical Biology at Cornell University. “This is challenging because a general and efficient way for making vicinal diamines is to directly install two carbon-nitrogen bonds onto an olefin; however, this process usually requires esoteric reagents or heavy metal catalysts, which are not sustainable and difficult to use on practical scales.”
To that end, Lin and his team set out to develop a practical and more environmentally friendly approach to manufacturing vicinal diamines, using a combination of electricity and a manganese catalyst to convert alkenes and sodium azide – both readily available feedstocks – into 1,2-diazides. The resultant 1,2-diazides were then smoothly reduced to vicinal diamines in a single step using standard protocols with high chemoselectivity (1).
Electrochemistry has yet to be broadly applied in organic synthesis, according to Lin; one reason being it can be challenging to work out which reaction conditions will allow electrochemistry and the molecular catalysis to act together in the correct manner. But the technique does offer the advantage of allowing researchers to fine-tune their reactions by altering the voltage, and thereby the electrical oxidation potential of a given reaction component. Such control allows researchers to target specific components, without disturbing other functional groups.
“We hope people will start to use this potentially enabling technology in both the large-scale manufacturing of drugs and also in the laboratory discovery of new medicines,” says Lin.
- N Fu et al., “Metal-catalyzed electrochemical diazidation of alkenes”, Science, 357 (6351), 575-579 (2017). PMID: 28798126.
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