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Synlett 2018; 29(13): 1765-1768
DOI: 10.1055/s-0037-1610086
DOI: 10.1055/s-0037-1610086
letter
Metal-free Reduction of Nitro Aromatics to Amines with B2(OH)4/H2O
National Natural Science Foundation of China (21202092). Startup Foundation from the China Three Gorges University (KJ2012B080, KJ2014H008).Further Information
Publication History
Received: 10 May 2018
Accepted after revision: 13.05,2018
Publication Date:
19 June 2018 (online)
![](https://www.thieme-connect.de/media/synlett/201813/lookinside/thumbnails/st-2018-w0195-l_10-1055_s-0037-1610086-1.jpg)
Abstract
A metal-free reduction of nitro aromatics mediated by diboronic acid with water as both the hydrogen donor and solvent under mild conditions has been developed. A series of aromatic amines were obtained with good functional group tolerance and in good yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610086.
- Supporting Information
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- 15 Aniline (2a) Nitrobenzene (123 mg, 1.0 mmol), B2(OH)4 (448 mg, 5.0 mmol, 5.0 equiv), and H2O (3.0 mL) were added to a 10 mL tube. The reaction mixture was stirred at 80 °C for 8 h. When the reaction was complete (monitored by TLC), the mixture was cooled to r.t. and extracted with ethyl acetate (3 × 20 mL). The combined organic phase was dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Colorless oil (92 mg, 99%); 1H NMR (400 MHz, CDCl3): δ = 7.27–7.22 (m, 2 H), 6.87–6.83 (m, 1 H), 6.76 (dd, J1 = 7.6 Hz, J2 = 0.8 Hz, 2 H), 3.66 (br, 2 H) ppm; 13C NMR (101 MHz, CDCl3): δ = 146.60, 129.49, 118.72, 115.30 ppm.
For a review on the advancement of methodologies for reduction of nitro aromatics, see: