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Synlett 2019; 30(07): 833-836
DOI: 10.1055/s-0037-1611749
DOI: 10.1055/s-0037-1611749
letter
Copper-Catalyzed Direct α-Nitration of Nitrostilbenes with Nitrogen Dioxide
Further Information
Publication History
Received: 25 December 2018
Accepted after revision: 08 February 2019
Publication Date:
15 March 2019 (online)
Abstract
A novel and efficient method for the direct α-nitration of nitrostilbenes was developed in which NO2 was used as the nitro source. This method provided (E)-α-nitrostilbenes derivatives in moderate to good yields. A broad substrate scope, mild and convenient conditions, and high stereoselectivity are important features of this method.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611749.
- Supporting Information
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References and Notes
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- 17 1,3,5-Trinitro-2-[(E)-1-nitro-2-phenylvinyl]benzene (2a): Typical Procedure A 35 mL sealed tube with a Teflon-lined cap was charged with 1,3,5-trinitro-2-[(E)-2-phenylvinyl]benzene (1a; 1 mmol), CuCl2∙2H2O (10 mol%), DCE (4 mL), and cold liquid NO2 (0.14 mL, 4 mmol). The tube was placed in an oil bath, which was stirred and heated at 60 °C for 3 h. The mixture was cooled to r.t., and the reaction was quenched with H2O. The resulting mixture was extracted with CH2Cl2 (3 × 30 mL), and the organic layers were combined, dried (Na2SO4), and concentrated under vacuum. The crude product was purified by column chromatography [silica gel, hexane–CH2Cl2 (2:3)] to give a yellow solid; yield: 274 mg (85%); mp 168–170 °C; Rf = 0.37 (CH2Cl2–hexane, 3:2). 1H NMR (300 MHz, DMSO-d 6): δ = 9.29 (s, 2 H), 8.71 (s, 1 H), 7.47 (d, J = 7.4 Hz, 1 H), 7.44–7.29 (m, 2 H), 7.20 (d, J = 7.4 Hz, 2 H). 13C NMR (126 MHz, DMSO-d 6): δ = 149.7, 149.6, 139.3, 138.9, 133.2, 131.5, 130.0, 129.1, 125.9, 124.5. HRMS (ESI-TOF): m/z [M + H]+ calcd. for C14H9N4O8: 361.0420; found 361.0413.
- 18 CCDC 1884696 contains the supplementary crystallographic data for compound 2b. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.