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

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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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
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spelling doaj-da275702b6d9498287479bc2a7057d0f2020-11-24T21:55:20ZengElsevierJournal of Saudi Chemical Society1319-61032019-11-01237896902Metal- and acid-free, TBN-mediated direct CH nitration of arenesGuangqiang Xu0Li Zhou1Chengdong Lv2Mo Xian3Qinggang Wang4Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, ChinaKey Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China; Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Sciences, Beijing 100049, ChinaKey Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China; Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Sciences, Beijing 100049, ChinaKey Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China; Corresponding authors.Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China; Corresponding authors.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 areneshttp://www.sciencedirect.com/science/article/pii/S131961031930002X
collection DOAJ
language English
format Article
sources DOAJ
author Guangqiang Xu
Li Zhou
Chengdong Lv
Mo Xian
Qinggang Wang
spellingShingle Guangqiang Xu
Li Zhou
Chengdong Lv
Mo Xian
Qinggang Wang
Metal- and acid-free, TBN-mediated direct CH nitration of arenes
Journal of Saudi Chemical Society
author_facet Guangqiang Xu
Li Zhou
Chengdong Lv
Mo Xian
Qinggang Wang
author_sort Guangqiang Xu
title Metal- and acid-free, TBN-mediated direct CH nitration of arenes
title_short Metal- and acid-free, TBN-mediated direct CH nitration of arenes
title_full Metal- and acid-free, TBN-mediated direct CH nitration of arenes
title_fullStr Metal- and acid-free, TBN-mediated direct CH nitration of arenes
title_full_unstemmed Metal- and acid-free, TBN-mediated direct CH nitration of arenes
title_sort metal- and acid-free, tbn-mediated direct ch nitration of arenes
publisher Elsevier
series Journal of Saudi Chemical Society
issn 1319-6103
publishDate 2019-11-01
description 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
url http://www.sciencedirect.com/science/article/pii/S131961031930002X
work_keys_str_mv AT guangqiangxu metalandacidfreetbnmediateddirectchnitrationofarenes
AT lizhou metalandacidfreetbnmediateddirectchnitrationofarenes
AT chengdonglv metalandacidfreetbnmediateddirectchnitrationofarenes
AT moxian metalandacidfreetbnmediateddirectchnitrationofarenes
AT qinggangwang metalandacidfreetbnmediateddirectchnitrationofarenes
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