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

Abstract

By synergizing the heterogeneous synthetic approach with the 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 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.