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Further insight into the photochemical behavior of 3-aryl-N-(arylsulfonyl)propiolamides: tunable synthetic route to phenanthrenes

Ming Chen,a  Xinxin Zhao,a  Chao Yang,a  Yanpei Wanga  and  Wujiong Xia*a 
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* Corresponding authors

a State Key Lab of Urban Water Resource and Environment, Shenzhen Graduate School, Harbin Institute of Technology, Harbin 150080, P. R. China
E-mail: xiawj@hit.edu.cn

Abstract

Reported herein is further insight into the photochemical behaviour of 3-aryl-N-(arylsulfonyl)-propiolamides, which provides a straightforward way to access meaningful phenanthrenes. Mechanistic investigation indicated that aryl migration, C–C coupling, 1,3-hydrogen shift, desulfonylation and elimination were involved in the process. Moreover, this protocol allowed for scale-up using a flow reactor.

Graphical abstract: Further insight into the photochemical behavior of 3-aryl-N-(arylsulfonyl)propiolamides: tunable synthetic route to phenanthrenes

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Publication details

The article was received on 05 Jan 2017, accepted on 09 Feb 2017 and first published on 20 Feb 2017


Article type: Paper
DOI: 10.1039/C7RA00193B
Citation: RSC Adv., 2017,7, 12022-12026
  • Open access: Creative Commons BY license
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    Further insight into the photochemical behavior of 3-aryl-N-(arylsulfonyl)propiolamides: tunable synthetic route to phenanthrenes

    M. Chen, X. Zhao, C. Yang, Y. Wang and W. Xia, RSC Adv., 2017, 7, 12022
    DOI: 10.1039/C7RA00193B

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