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

Abstract

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