Current study opens new possibilities for nitrogen chemistry

Nitrogen atoms are essential building blocks in many important chemical structures. Nitrogen-containing organic molecules are indispensable for various applications in such fields as medicine, agriculture and materials science. To produce such compounds, various proven methods are used that reliably form carbon-nitrogen bonds. In contrast, the so-called hydroamidation of a widely used class of carbon compounds, alkenes, has remained an underutilised approach. Prof Armido Studer's group at the Institute of Organic Chemistry at the University of Münster (Germany) has now developed an iron-catalysed radical hydroamidation reaction. It efficiently introduces nitrogen-containing molecular moieties (amides) into organic molecules that contain double bonds as chemically modifiable groups.

‘The new method has a broad scope and enables the hydroamidation of complex natural products such as terpenes,’ explains Armido Studer. At the heart of the reaction is a novel amidation reagent that facilitates the transfer of the cyanamide functional group to the desired chemical bond used in the manufacture of numerous products in the chemical industry. The reagent can be prepared on a larger scale, making the process attractive for industrial applications.

Beyond its direct applications, this method, which is described in the journal Nature Synthesis, unlocks new possibilities for catalysing chemical transformations. ‘The introduced cyanamide functional group can be readily converted to other useful groups. This highlights the versatility and impact of this strategy,’ says Mengjun Huang, who conducted the experimental studies. By expanding the toolbox for nitrogen incorporation, this discovery paves the way for more efficient and sustainable chemical synthesis.