Synthesis of N-Heteroarenemethyl Esters via C-C Bond Cleavage of Acyl Cyanides Under Transition Metal-Free Conditions

Miao Lai; Fangyao Su; Jingyi Hu; Mengzhuo Wang; Mingqin Zhao; Ganlin Zhang

doi:10.3389/fchem.2021.822625

Synthesis of N-Heteroarenemethyl Esters via C-C Bond Cleavage of Acyl Cyanides Under Transition Metal-Free Conditions

Front Chem. 2022 Jan 27:9:822625. doi: 10.3389/fchem.2021.822625. eCollection 2021.

Authors

Miao Lai¹, Fangyao Su¹, Jingyi Hu¹, Mengzhuo Wang¹, Mingqin Zhao¹, Ganlin Zhang¹

Affiliation

¹ Flavors and Fragrance Engineering and Technology Research Center of Henan Province, College of Tobacco Science, Henan Agricultural University, Zhengzhou, China.

Abstract

A practical method to synthesize N-heteroaryl esters from N-heteroaryl methanols with acyl cyanides via C-C bond cleavage without using any transition metal is demonstrated here. The use of Na₂CO₃/15-crown-5 couple enables access to a series of N-heteroaryl esters in high efficiency. This protocol is operationally simple and highly environmentally benign producing only cyanides as byproducts.

Keywords: C-C bond cleavage; N-heteroaryl esters; N-heteroaryl methanols; acyl cyanides; transition-metal free synthesis.