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Synlett 2019; 30(02): 193-198
DOI: 10.1055/s-0037-1611695
letter
© Georg Thieme Verlag Stuttgart · New York

A Newly Designed Carbohydrate-Derived Alkylamine Promotes Ullmann Type C–N Coupling Catalyzed by Copper in Water

Guoquan Zhou
a   School of Material and Chemical Engineering, Ningbo University of Technology, Ningbo, P. R. of China
c   Department of Chemistry, Prairie View A&M University, Prairie View, USA   Email: hjfan@pvamu.edu
,
Wen Chen
b   School of Chemical and Material Engineering, Jiangnan University, Wuxi, P. R. of China   Email: gexin@jiangnan.edu.cn
,
Shihui Zhang
b   School of Chemical and Material Engineering, Jiangnan University, Wuxi, P. R. of China   Email: gexin@jiangnan.edu.cn
,
Xuemin Liu
b   School of Chemical and Material Engineering, Jiangnan University, Wuxi, P. R. of China   Email: gexin@jiangnan.edu.cn
,
Zehui Yang
a   School of Material and Chemical Engineering, Ningbo University of Technology, Ningbo, P. R. of China
,
Xin Ge*
b   School of Chemical and Material Engineering, Jiangnan University, Wuxi, P. R. of China   Email: gexin@jiangnan.edu.cn
,
Hua-Jun Fan*
c   Department of Chemistry, Prairie View A&M University, Prairie View, USA   Email: hjfan@pvamu.edu
› Author AffiliationsThis research is sponsored by China National Key Research and invention program of the thirteenth Five-Year Plan (2017YFD0200707), the Natural Science Foundation of China (21606104), the Opening Foundation from Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology (ACEMT-17-03) and US Department of Energy, National Nuclear Security Administration grant (DE-NA 0001861 & DE-NA 0002630).
Further Information

Publication History

Received: 07 October 2018

Accepted after revision: 25 November 2018

Publication Date:
17 December 2018 (online)

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Abstract

A green and biodegradable carbohydrate-derived alkylamine was designed and employed as ligand for Ullmann type C–N coupling catalyzed by copper in water. The coupling of aryl iodide and N-nucleophiles were examined and moderate to excellent yields were obtained. In addition, the in-water coupling strategy was expanded successfully to the reaction of indoles with 4-iodoanisole. By measuring the solubility, it is speculated that carbohydrate-derived alkylamine plays the role of chelating copper and promoting the dissolution of 4-iodoanisole in water. Remarkably, this methodology was environmentally friendly and economical because of the use of aqueous media in place of organic solvents.

Key words

glycosyl ligand - in water - copper - Ullmann reaction - green chemistry

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611695.
  • Supporting Information
 

  • References and Notes

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