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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 10
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Original Articles

p-Toluenesulfonic acid-promoted autocatalytic hydrolyzation of 1-tosyl-1,2,3-triazoles

Haohao DongKey Laboratory for Advanced Materials, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai, P. R. ChinaView further author information
,
Dongdong ZhangKey Laboratory for Advanced Materials, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai, P. R. ChinaView further author information
,
Renjie FangKey Laboratory for Advanced Materials, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai, P. R. ChinaView further author information
,
Qingyang DuKey Laboratory for Advanced Materials, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai, P. R. ChinaView further author information
,
Zhuoya DongKey Laboratory for Advanced Materials, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai, P. R. ChinaView further author information
,
Hao WeiKey Laboratory for Thin Film and Microfabrication Technology of Ministry of Education, School of Electronic Information and Electrical Engineering, Shanghai Jiao Tong University, Shanghai, P. R. ChinaCorrespondence[email protected]
View further author information
,
Min ShiKey Laboratory for Advanced Materials, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai, P. R. China;State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Shanghai, P. R. ChinaView further author information
&
Feijun WangKey Laboratory for Advanced Materials, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai, P. R. ChinaCorrespondence[email protected]
View further author information
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Pages 1227-1234 | Received 03 Dec 2017, Published online: 02 Apr 2018
 
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ABSTRACT

The first example of autocatalytic hydrolyzation of 4-aryl-1-tosyl-1,2,3-triazoles induced by p-toluenesulfonic acid was reported, providing an effective and metal-free synthetic approach to deliver a broad range of new 4-aryl-2H-1,2,3-triazoles in good yields. The kinetic profile of this hydrolyzation suggested that this reaction has exponential autocatalytic behavior.

GRAPHICAL ABSTRACT

Additional information

Funding

We are grateful for the financial support from the National Natural Science Foundation of China (21372075, 81670958, and 81371178), the Shanghai Pujiang Program (16PJD017 and 16PJD027), and the Medical-Engineering Crossover Fund of Shanghai Jiao Tong University (YG2015MS23 and YG2016MS71).

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