CN and NH Bond Metathesis Reactions Mediated by Carbon Dioxide. Issue 12 (3rd June 2015)

• Record Type: Journal Article
• Authors: Wang, Yehong; Zhang, Jian; Liu, Jing; Zhang, Chaofeng; Zhang, Zhixin; Xu, Jie; Xu, Shutao; Wang, Fangjun; Wang, Feng
• Is Part Of: ChemSusChem. Volume 8:Issue 12(2015:Jun.)
• Page Start: 2066
• Page End: 2072
• Publication Date: 2015-06-03
• Subjects: Green chemistry -- Periodicals; Sustainable engineering -- Periodicals; Chemistry -- Periodicals; Chemical engineering -- Periodicals; 660
• DOI: 10.1002/cssc.201500318
• Languages: English
• ISSNs: 1864-5631

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Herein, we report CO₂‐mediated metathesis reactions between amines and DMF to synthesize formamides. More than 20 amines, including primary, secondary, aromatic, and heterocyclic amines, diamines, and amino acids, are converted to the corresponding formamides with good‐to‐excellent conversions and selectivities under mild conditions. This strategy employs CO₂ as a mediator to activate the amine under metal‐free conditions. The experimental data and in situ NMR and attenuated total reflectance IR spectroscopy measurements support the formation of the <italic>N</italic>‐carbamic acid as an intermediate through the weak acid–base interaction between CO₂ and the amine. The metathesis reaction is driven by the formation of a stable carbamate, and a reaction mechanism is proposed.</p> </abstract>