From Dinitrogen to N‐Containing Organic Compounds: Using Li2CN2 as a Synthon

Author:

Wu Li‐Jun1,Wang Qianru23,Guo Jianping23,Wei Junnian1,Chen Ping234,Xi Zhenfeng15ORCID

Affiliation:

1. Beijing National Laboratory for Molecular Sciences (BNLMS) Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education College of Chemistry Peking University Beijing 100871 China

2. Dalian Institute of Chemical Physics Chinese Academy of Sciences Dalian 116023 China

3. University of Chinese Academy of Sciences Beijing 100049 China

4. State Key Laboratory of Catalysis Dalian Institute of Chemical Physics Dalian 116023 China

5. State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Shanghai 200032 China

Abstract

AbstractThrough the synergies of a heterogeneous synthetic approach and a homogeneous synthetic methodology, N‐containing organic compounds can be synthesized via activated N‐containing species prepared from N2 gas and suitable carbon sources. From N2, carbon, and LiH, we have previously succeeded in the high‐yield preparation of Li2CN2 as the activated N‐containing species. In this work, we applied Li2CN2 as a novel synthetic synthon for constructing N‐containing organic compounds. A series of reaction models, including a substitution reaction, cycloaddition reaction, and transition metal‐catalyzed coupling reaction, were successfully performed using Li2CN2 under mild conditions. Various valuable cyanamides, carbodiimides, N‐aryl cyanamides and 1,2,4‐triazole derivatives were readily synthesized in moderate to excellent yields. With this method, the 15N‐labeled products, including oxazolidine derivatives with anti‐cancer activity, could also be facilely prepared from 15N2 gas.

Funder

National Natural Science Foundation of China

Natural Science Foundation of Beijing Municipality

China Postdoctoral Science Foundation

Publisher

Wiley

Subject

General Chemistry,Catalysis

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