Synthesis of alkyl amines from dinitrogen and alkenes succeeded

June 18, 2024

Molecular activation and transformation using titanium polyhydrides

An international joint group of researchers from the RIKEN CSRS, the RIKEN Cluster for Pioneering Research, Saitama University, and Anhui University successfully synthesized various alkyl amines (R-NH₂) directly from highly stable nitrogen molecules (N₂) and simple feedstock alkenes using titanium polyhydrides under mild reaction conditions.

Alkyl amines represent an important class of compounds that can be widely used for many purposes. Containing nitrogen and carbon, they are generally synthesized from ammonia (NH₃) or nitrogen sources derived from NH₃, and prefunctionalized carbon sources, such as alcohols (R-OH) or carboxylic compounds (R-C(＝O)OH). However, preparatioin of these nitrogen and carbon sources from abundant and readily accessible N₂ and simple alkenes consumes much energy. The synthesis of alkyl amines directly from N₂ and alkenes is intriguing from a synthetic chemical perspective but remains a challenge.

In this study, the research group used titanium hydride compounds that the researchers had developed by themselves and successfully synthesized alkyl amines under mild conditions (normal temperature and pressure) by breaking C-H bonds in simple alkenes and N≡N bonds in N₂, leading to the selective formation of N-C bonds. They also elucidated its reaction process at a molecular level using X-ray crystallography, spectroscopy, and computational chemistry.

The results of this study are expected to lead to the development of strategies to synthesize various nitrogen-containing organic compounds directly from nitrogen molecules and simple hydrocarbons.

Original article

Nature doi: 10.1038/s41586-024-07694-5

T. Shima, Q. Zhuo, X. Zhou, P. Wu, R. Owada, G. Luo, Z. Hou,

"Hydroamination of alkenes with dinitrogen and titanium polyhydrides".

Contact

Takanori Shima; Senior Research Scientist
Zhaomin Hou; Group Director
Advanced Catalysis Research Group