Direct N-Alkylation/Fluoroalkylation of Amines Using Carboxylic Acids via Transition-Metal-Free Catalysis was written by Lu, Chunlei;Qiu, Zetian;Xuan, Maojie;Huang, Yan;Lou, Yongjia;Zhu, Yiling;Shen, Hao;Lin, Bo-Lin. And the article was included in Advanced Synthesis & Catalysis in 2020.Reference of 4714-63-0 This article mentions the following:
A scalable protocol of direct N-mono/di-alkyl/fluoroalkylation of primary/secondary amines was constructed with various carboxylic acids as coupling agents under the catalysis of a simple air-tolerant inorganic salt, K3PO4. Advantageous features include 100 examples, 10 drugs and drug-like amines, fluorinated complex tertiary amines, gram-scale synthesis and isotope-labeling amine, thus demonstrating the potential applicability in industry of this methodol. The involvement of relatively less reactive silicon-hydride compared with the traditional reactive metal-hydride or boron-hydride species required to reduce the amide intermediates presumably contributes to the remarkable functional group compatibility. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0Reference of 4714-63-0).
4-(Ethylamino)benzonitrile (cas: 4714-63-0) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Reference of 4714-63-0
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts