Transition-Metal-Free Deacylative Cleavage of Unstrained C(sp3)–C(sp2) Bonds: Cyanide-Free Access to Aryl and Aliphatic Nitriles from Ketones and Aldehydes

A transition-metal-free deacylative C­(sp3)–C­(sp2) 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...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2016-01, Vol.18 (2), p.228-231
Main Authors: Ge, Jing-Jie, Yao, Chuan-Zhi, Wang, Mei-Mei, Zheng, Hong-Xing, Kang, Yan-Biao, Li, Yadong
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A transition-metal-free deacylative C­(sp3)–C­(sp2) 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b03367