Diastereodivergent Intermolecular 1,2-Diamination of Unactivated Alkenes Enabled by Iodine Catalysis

A dab of iodine for drug synthesis

30 June 2021

A green method has been developed for a selectively synthesising the common ‘1,2-dimanine’ structural motif, found in many biologically active organic molecules.

From drug molecules to organocatalysts, many valuable organic molecules contain a pair of nitrogen atoms attached to two adjacent carbon atoms in their structure. Although such 1,2-diamines can be made from alkenes in a metal-catalysed process, the nitrogen atoms in the product often tightly bind with the metal, making removing the catalyst very costly.

Now, a team of five researchers at Osaka University in Japan has developed an iodine-catalysed protocol to produce 1,2-diamines from alkenes.

The metal-free method generates a reactive nitrogen-iodine intermediate to install the nitrogen atoms. Depending on the nitrogen starting material, researchers can choose to install the nitrogen atoms on the same or opposite faces of the molecule, and the only reaction by-products are sodium chloride and water.

Supported content

References

1. Journal of the American Chemical Society 143, 4112–4118 (2021). doi: 10.1021/jacs.1c00228