Synthesis of arylamines and N-heterocycles by direct catalytic nitrogenation using N2

Ammonia and nitric acid are two key platform chemicals to introduce nitrogen atoms into organic molecules in chemical industry. Indeed, nitric acid is mostly produced through the oxidation of ammonia. The ideal nitrogenation would involve direct use of dinitrogen (N 2 ) as a N source to construct N-...

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Bibliographic Details
Published in:Nature communications 2021-01, Vol.12 (1), p.248-248, Article 248
Main Authors: Wang, Kai, Deng, Zi-Hao, Xie, Si-Jun, Zhai, Dan-Dan, Fang, Hua-Yi, Shi, Zhang-Jie
Format: Article
Language:English
Subjects:
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140/146
639/638/549/884
639/638/549/933
639/638/77/888
Amines
Ammonia
Chemical industry
Chemical synthesis
Chemicals
Humanities and Social Sciences
Lithium
multidisciplinary
Nitric acid
Nitrogen
Nitrogen atoms
Nitrogenation
Organic chemistry
Organic compounds
Oxidation
Polyanilines
Reducing agents
Science
Science (multidisciplinary)
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Summary:Ammonia and nitric acid are two key platform chemicals to introduce nitrogen atoms into organic molecules in chemical industry. Indeed, nitric acid is mostly produced through the oxidation of ammonia. The ideal nitrogenation would involve direct use of dinitrogen (N 2 ) as a N source to construct N-containing organic molecules. Herein, we report an example of direct catalytic nitrogenation to afford valuable diarylamines, triarylamines, and N-heterocycles from easily available organohalides using dinitrogen (N 2 ) as the nitrogen source in a one-pot/two-step protocol. With this method, 15 N atoms are easily incorporated into organic molecules. Structurally diversified polyanilines are also generated in one pot, showing great potential for materials chemistry. In this protocol, lithium nitride, generated in situ with the use of lithium as a reductant, is confirmed as a key intermediate. This chemistry provides an alternative pathway for catalytic nitrogenation to synthesize highly valuable N-containing chemicals from dinitrogen. Ammonia and nitric acid are key platform chemicals to introduce nitrogen into organic molecules, however gaseous N 2 would be a more direct and available source of nitrogen. Here, the authors report a direct catalytic nitrogenation to afford valuable arylamines and N-heterocycles from organohalides using dinitrogen (N 2 ) as the nitrogen source.
ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-020-20270-5