Journal
SYNLETT
Volume 30, Issue 2, Pages 193-198Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1611695
Keywords
glycosyl ligand; in water; copper; Ullmann reaction; green chemistry
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Funding
- China National Key Research and invention program of the thirteenth Five-Year Plan [2017YFD0200707]
- Natural Science Foundation of China [21606104]
- Opening Foundation from Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology [ACEMT-17-03]
- US Depart-ment of Energy, National Nuclear Security Administration grant [DENA 0001861, DE-NA 0002630]
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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.
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