Metal- and acid-free, TBN-mediated direct CH nitration of arenes

A metal-free, acid-free, direct and eco-friendly nitration methodology has been developed. A tert-butyl nitrite efficiently promotes the direct CH nitration of electron-rich arenes with good to excellent yields and regioselectivities. The practical utility of this protocol has been demonstrated in...

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Bibliographic Details
Main Authors: Guangqiang Xu, Li Zhou, Chengdong Lv, Mo Xian, Qinggang Wang
Format: Article
Language:English
Published: Elsevier 2019-11-01
Series:Journal of Saudi Chemical Society
Online Access:http://www.sciencedirect.com/science/article/pii/S131961031930002X
Description
Summary:A metal-free, acid-free, direct and eco-friendly nitration methodology has been developed. A tert-butyl nitrite efficiently promotes the direct CH nitration of electron-rich arenes with good to excellent yields and regioselectivities. The practical utility of this protocol has been demonstrated in gram-scale nitration of crown ether and mono nitration of Sesamin. A plausible free radical mechanism is proposed based on detailed experimental observations. Keywords: Metal-free, Acid-free, Tert-butyl nitrite, Nitration, Electron-rich arenes
ISSN:1319-6103