Literature DB >> 25338129

Mild Cu(I)-catalyzed cascade reaction of cyclic diaryliodoniums, sodium azide, and alkynes: efficient synthesis of triazolophenanthridines.

Zhenquan Liu1, Daqian Zhu, Bingling Luo, Naiyuan Zhang, Qi Liu, Yumin Hu, Rongbiao Pi, Peng Huang, Shijun Wen.   

Abstract

Linear iodoniums are widely used as arylating reagents. However, cyclic diaryl idodoniums are ignored despite their potential to initiate dual arylations, atom and step economically. In our current work, a three-component cascade reaction of cyclic diaryliodoniums, sodium azide, and alkynes has been successfully achieved under mild conditions, catalyzed by cheap copper species. The regioselectivity associated with unsymmetrical iodoniums was enhanced by installing two methyls ortho and para to the I(III) center. The reaction enables a rapid access to a variety of complex molecules, triazolophenanthridine derivatives.

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Year:  2014        PMID: 25338129     DOI: 10.1021/ol502654a

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

Review 1.  Metal-Catalysed Azidation of Organic Molecules.

Authors:  Monalisa Goswami; Bas de Bruin
Journal:  European J Org Chem       Date:  2016-12-22

2.  Highly Reactive Cyclic Monoaryl Iodoniums Tuned as Carbene Generators Couple with Nucleophiles under Metal-Free Conditions.

Authors:  Haiwen Wang; Liyun Liang; Zhirong Guo; Hui Peng; Shuang Qiao; Nemai Saha; Daqian Zhu; Wenbin Zeng; Yunyun Chen; Peng Huang; Shijun Wen
Journal:  iScience       Date:  2020-06-23

3.  Heterocyclic iodoniums as versatile synthons to approach diversified polycyclic heteroarenes.

Authors:  Daqian Zhu; Zhouming Wu; Liyun Liang; Yameng Sun; Bingling Luo; Peng Huang; Shijun Wen
Journal:  RSC Adv       Date:  2019-10-16       Impact factor: 4.036

4.  Design, synthesis and biological evaluation of N-arylsulfonyl carbazoles as novel anticancer agents.

Authors:  Xin You; Daqian Zhu; Wenhua Lu; Yichen Sun; Shuang Qiao; Bingling Luo; Yongliang Du; Rongbiao Pi; Yumin Hu; Peng Huang; Shijun Wen
Journal:  RSC Adv       Date:  2018-05-10       Impact factor: 3.361

Review 5.  Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis.

Authors:  Gwendal Grelier; Benjamin Darses; Philippe Dauban
Journal:  Beilstein J Org Chem       Date:  2018-06-21       Impact factor: 2.883

  5 in total

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