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Synlett 2019; 30(02): 193-198
DOI: 10.1055/s-0037-1611695
DOI: 10.1055/s-0037-1611695
letter
A Newly Designed Carbohydrate-Derived Alkylamine Promotes Ullmann Type C–N Coupling Catalyzed by Copper in Water
This 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)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611695.
- Supporting Information
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- 33 Preparation of N,N′-Di-β-d-glucopyansoyl Ethylenediamine L5 A mixture of glucose (3.6 g, 20 mmol), ethylenediamine (0.6 g, 10 mmol) and acetic acid (0.1 g, 1.67 mmol) in CH3OH was heated at reflux at 30 °C. After 8 h the solvent was removed under vacuum. The pure product L5 was recrystallized in ethanol as a white solid. Mp 125.3–126.1 °C. [α]D 20 = –29.6 (c 1.00, H2O). 1H NMR (600 MHz, D2O): δ = 3.92 (d, J = 8.0 Hz, 2 H), 3.80 (d, J = 11.8 Hz, 2 H), 3.69–3.55 (m, 2 H), 3.37 (d, J = 8.0 Hz, 2 H), 3.33–3.20 (m, 4 H), 3.11 (t, J = 8.2 Hz, 2 H), 2.89 (d, J = 6.4 Hz, 2 H), 2.74 (d, J = 6.8 Hz, 2 H). 13C NMR (150 MHz, D2O): δ = 89.73, 76.77, 76.68, 72.94, 69.84, 60.86, 44.89. 1 J[13CH(1)]=151.5. IR (KBr): 3290 and 3230 [ν(O-H)], 2877 [ν(C-H)], 1469 and 1361 [δ(C-H)], 1268 [ν(C-O-C)], 1076 and 1014 [ν(C-N)], 811 [δ(N-H)]. MS (EI): m/z = 384 [M]+.
- 34 CuI/L5 Catalyzed Ullmann Type C–N Coupling of Aryl Halides and Nitrogen Nucleophiles in Water; General Procedure To a stirred solution of H2O (5 mL) were added CuI (0.1 mmol, 19 mg), aryl halide (1.0 mmol), nitrogen nucleophile (1.2 mmol), Cs2CO3 (2 mmol, 651 mg) and L5 (0.1 mmol), and the mixture was heated to 100 °C under air and stirred for 24 h. When the reaction was complete, the mixture was cooled and partitioned by adding ethyl acetate (20 mL) and water (20 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (2 × 20 mL). The combined organic phases were washed with saturated brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by column chromatography through silica gel, eluting with ethyl acetate/petroleum ether solvent mixture, to give the pure product. Data for 1-(4-Methoxyphenyl)-1H-imidazole 3a as Typical Example Pale-yellow solid; mp 60–61 °C. 1H NMR (400 MHz, CDCl3): δ = 7.79 (s, 1 H), 7.30 (d, J = 8.8 Hz, 2 H), 7.20 (d, J = 6.6 Hz, 2 H), 6.99 (d, J = 12.0 Hz, 2 H), 3.85 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 159.0, 135.8, 130.7, 129.9, 123.3, 118.8, 114.9, 55.6. MS (EI): m/z = 174 [M]+ .