Transition-Metal-Free Deacylative Cleavage of Unstrained C(sp(3))-C(sp(2)) Bonds: Cyanide-Free Access to Aryl and Aliphatic Nitriles from Ketones and Aldehydes

Jing-Jie Ge; Chuan-Zhi Yao; Mei-Mei Wang; Hong-Xing Zheng; Yan-Biao Kang; Yadong Li

doi:10.1021/acs.orglett.5b03367

Transition-Metal-Free Deacylative Cleavage of Unstrained C(sp(3))-C(sp(2)) Bonds: Cyanide-Free Access to Aryl and Aliphatic Nitriles from Ketones and Aldehydes

Org Lett. 2016 Jan 15;18(2):228-31. doi: 10.1021/acs.orglett.5b03367. Epub 2015 Dec 24.

Authors

Jing-Jie Ge¹, Chuan-Zhi Yao¹, Mei-Mei Wang¹, Hong-Xing Zheng¹, Yan-Biao Kang¹, Yadong Li^{1

2}

Affiliations

¹ Center of Advanced Nanocatalysis, Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, China.
² Department of Chemistry, Collaborative Innovation Center for Nanomaterial Science and Engineering, Tsinghua University , Beijing 100084, China.

PMID: 26704699
DOI: 10.1021/acs.orglett.5b03367

Abstract

A transition-metal-free deacylative C(sp(3))-C(sp(2)) bond cleavage for the synthetically practical oxidative amination of ketones and aldehydes to nitriles is first described, using cheap and commercially abundant NaNO2 as the oxidant and the nitrogen source. Various nitriles bearing aryl, heteroaryl, alkyl, and alkenyl groups could be smoothly obtained from ketones and aldehydes in high yields, avoiding highly toxic cyanides or transition metals.

Publication types

Research Support, Non-U.S. Gov't