Metal- and Acid-Free, TBN-Mediated Direct C–H Nitration of Arenes

Publication date: Available online 18 January 2019Source: Journal of Saudi Chemical SocietyAuthor(s): Guangqiang Xu, Li Zhou, Chengdong Lv, Mo Xian, Qinggang WangAbstractA 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.Graphical abstract
Source: Journal of Saudi Chemical Society - Category: Chemistry Source Type: research