An Efficient Protocol for the Synthesis of O-Fluoroalkylisoureas through Copper-Catalysed, Three-Component Reaction of Cyan­amides, Fluoroalcohols and Diaryliodonium Triflates

Jihui Li; Weiguang Yu; Yifeng Hou; Wenxing Fu; Shuying Xu; Yucang Zhang

doi:10.1055/s-0036-1590828

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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

^aKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources in Hainan University, Haikou 570228, P. R. of China

^bCollege 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

^aKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources in Hainan University, Haikou 570228, P. R. of China

^bCollege 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

^aKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources in Hainan University, Haikou 570228, P. R. of China

^bCollege 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

^aKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources in Hainan University, Haikou 570228, P. R. of China

^bCollege 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*

^aKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources in Hainan University, Haikou 570228, P. R. of China

^bCollege 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*

^aKey Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources in Hainan University, Haikou 570228, P. R. of China

^bCollege of Materials and Chemical Engineering, Hainan University, Haikou 570228, P. R. of China Email: xushuying1980@hainu.edu.cn Email: yczhang@hainu.edu.cn

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Abstract

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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

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References

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Supplementary Material

Supporting Information

An Efficient Protocol for the Synthesis of O-Fluoroalkylisoureas through Copper-Catalysed, Three-Component Reaction of Cyan­amides, Fluoroalcohols and Diaryliodonium Triflates

An Efficient Protocol for the Synthesis of O-Fluoroalkylisoureas through Copper-Catalysed, Three-Component Reaction of Cyanamides, Fluoroalcohols and Diaryliodonium Triflates