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CC BY ND NC 4.0 · SynOpen 2017; 01(01): 0076-0083
DOI: 10.1055/s-0036-1590828
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An Efficient Protocol for the Synthesis of O-Fluoroalkylisoureas through Copper-Catalysed, Three-Component Reaction of Cyan­amides, Fluoroalcohols and Diaryliodonium Triflates

Jihui Li
a   Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources in Hainan University, Haikou 570228, P. R. of China
b   College of Materials and Chemical Engineering, Hainan University, Haikou 570228, P. R. of China   eMail: xushuying1980@hainu.edu.cn   eMail: yczhang@hainu.edu.cn
,
Weiguang Yu
a   Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources in Hainan University, Haikou 570228, P. R. of China
b   College of Materials and Chemical Engineering, Hainan University, Haikou 570228, P. R. of China   eMail: xushuying1980@hainu.edu.cn   eMail: yczhang@hainu.edu.cn
,
Yifeng Hou
a   Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources in Hainan University, Haikou 570228, P. R. of China
b   College of Materials and Chemical Engineering, Hainan University, Haikou 570228, P. R. of China   eMail: xushuying1980@hainu.edu.cn   eMail: yczhang@hainu.edu.cn
,
Wenxing Fu
a   Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources in Hainan University, Haikou 570228, P. R. of China
b   College of Materials and Chemical Engineering, Hainan University, Haikou 570228, P. R. of China   eMail: xushuying1980@hainu.edu.cn   eMail: yczhang@hainu.edu.cn
,
Shuying Xu*
a   Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources in Hainan University, Haikou 570228, P. R. of China
b   College of Materials and Chemical Engineering, Hainan University, Haikou 570228, P. R. of China   eMail: xushuying1980@hainu.edu.cn   eMail: yczhang@hainu.edu.cn
,
Yucang Zhang*
a   Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources in Hainan University, Haikou 570228, P. R. of China
b   College of Materials and Chemical Engineering, Hainan University, Haikou 570228, P. R. of China   eMail: xushuying1980@hainu.edu.cn   eMail: yczhang@hainu.edu.cn
› Institutsangaben
The authors acknowledge the Natural Science Foundation of Hainan Province (grant numbers 20162015, 20152027), the National Natural Science Foundation of China (51263006) and Hainan Province International Science and Technology Specific (KJHZ2014-02) for financial support of this work
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Publikationsverlauf

Received: 15. Mai 2017

Accepted after revision: 20. Juni 2017

Publikationsdatum:
08. August 2017 (online)

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Abstract

A copper-catalysed, three-component reaction involving cyan­amides, fluoroalcohols and diaryliodonium triflates is disclosed for the synthesis of O-fluoroalkylisoureas. Various O-fluoroalkylisoureas were obtained in good yields by using simple and readily available substrates. Moreover, C–H activation of O-fluoroalkylisoureas mediated by PhI(OAc)2 was established to obtain 2-fluoroalkoxybenzimidazoles in high yields at room temperature.

Key words

copper-catalysis - three-component reaction - O-fluoro­alkylisourea - 2-alkoxybenzimidazole - C–H activation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590828.
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