Issue 7, 2017
From the journal:

Organic Chemistry Frontiers

Radical cyclization of benzene-tethered 1,7-enynes with aryldiazonium tetrafluoroborates: a facile route to benzo[j]phenanthridines†

Yuanyuan An,a   Jun Zhang,a   Hongguang Xia*b  and  Jie Wu*ac  

* Corresponding authors

a Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China
E-mail: jie_wu@fudan.edu.cn

b Department of Biochemistry and Molecular Biology, Zhejiang University School of Medicine, Hangzhou 310058, China
E-mail: hongguangxia@zju.edu.cn

c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China

Abstract

A radical cyclization of benzene-tethered 1,7-enynes with aryldiazonium tetrafluoroborates in the presence of copper(II) acetate and DABCO˙(SO2)2 is developed. This transformation is triggered by arylsulfonyl radicals which are generated in situ from aryldiazonium tetrafluoroborates and DABCO˙(SO2)2. This procedure is compatible with a wide range of functional groups, providing a facile route for the synthesis of diverse benzo[j]phenanthridines.

Graphical abstract: Radical cyclization of benzene-tethered 1,7-enynes with aryldiazonium tetrafluoroborates: a facile route to benzo[j]phenanthridines

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Article information

DOI
https://doi.org/10.1039/C7QO00193B
Article type
Research Article
Submitted
11 Mar 2017
Accepted
31 Mar 2017
First published
05 Apr 2017

Org. Chem. Front., 2017,4, 1318-1321

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Radical cyclization of benzene-tethered 1,7-enynes with aryldiazonium tetrafluoroborates: a facile route to benzo[j]phenanthridines

Y. An, J. Zhang, H. Xia and J. Wu, Org. Chem. Front., 2017, 4, 1318 DOI: 10.1039/C7QO00193B

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