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Synthesis 2018; 50(15): 2891-2896
DOI: 10.1055/s-0037-1610038
special topic
© Georg Thieme Verlag Stuttgart · New York

Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols

Qi Zhang
a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China   Email: bixh507@nenu.edu.cn
,
Kaki Raveendra Babu
a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China   Email: bixh507@nenu.edu.cn
,
Zhouliang Huang
b   College of Life Sciences, Jilin University, 2699 Qianjin Street, 130012 Changchun, P. R. of China
,
Jinna Song*
b   College of Life Sciences, Jilin University, 2699 Qianjin Street, 130012 Changchun, P. R. of China
,
Xihe Bi  *
a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China   Email: bixh507@nenu.edu.cn
c   State Key Laboratory of Elemento-Organic Chemistry, Nankai University, 94 Weijin Road, 300071 Tianjin, P. R. of China
› Author AffiliationsThis work was supported by the NSFC (21522202, 21502017, 21702028).
Further Information

Publication History

Received: 26 February 2018

Accepted after revision: 02 May 2018

Publication Date:
13 June 2018 (online)

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Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis

Abstract

We report a visible light-assisted one-pot method for the synthesis of polynitrophenols through radical tandem hydroxylation and nitration of arylboronic acids by utilizing copper(II) nitrate tri­hydrate as the nitro source. This method features mild conditions, a simple procedure, and good functional group tolerance. Compared to conventional methods, this work provides a straightforward approach for the polynitration of aromatic compounds.

Key words

polynitrophenols - visible light - arylboronic acid - nitration - copper

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610038.
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