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Synlett 2019; 30(14): 1683-1687
DOI: 10.1055/s-0037-1611761
DOI: 10.1055/s-0037-1611761
cluster
Diphenyl Diselenide Catalyzed Oxidative Degradation of Benzoin to Benzoic Acid
This work was financially supported by National Key Research and Development Program of China (2018YFD0200100), the Open Project Program of Jiangsu Key Laboratory of Zoonosis (R1609), Opening Foundation of the Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University (2016GDGP0104) and Priority Academic Program Development of Jiangsu Higher Education Institutions.Further Information
Publication History
Received: 07 January 2019
Accepted after revision: 27 February 2019
Publication Date:
02 April 2019 (online)
Published as part of the Cluster Organosulfur and Organoselenium Compounds in Catalysis
Abstract
The diphenyl diselenide catalyzed oxidative degradation of benzoin to benzoic acid is reported. As this reaction can convert the malodorous compound into an odorless and innocuous product under mild conditions, it might be useful for pollutant disposal. The reaction does not require a transition-metal catalyst or a chemical oxidant, so that it can be performed at low cost and without generation of wastes. This is believed to be the first example of the use of organoselenium catalysis technology in pollutant destruction, thereby expanding its range of applications.
Key words
diphenyl diselenide - organoselenium catalysis - green chemistry - benzoin - pollutant destruction - benzoinSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611761.
- Supporting Information
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- 11 Oxidation of Benzoin (1a) to Benzoic Acid (2a); Typical Procedure A reaction tube was charged with benzoin (1a; 212.2 mg, 1 mmol), (PhSe)2 (15.6 mg, 0.05 mmol), and a magnetic stirrer bar. A 30% aq solution of H2O2 (453.5 mg, 4 mmol) in MeCN (2 mL) was then injected into the tube from a syringe, and the mixture was stirred at r.t. for 24 h. The solvent was then evaporated under vacuum, and the residue was purified by preparative TLC (PE–EtOAc, 10:1) to give benzoic acid (2a) as a white solid; yield: 200.2 mg (82%); mp 122.0–122.4 °C (Lit.12a 122.13 °C). IR (KBr): 1915, 1680, 1485, 1455, 1398, 1324, 1291, 1181, 933, 805 cm–1. 1H NMR (400 MHz, CDCl3, TMS): δ = 8.13 (d, J = 8.9 Hz, 2 H), 7.62 (t, J = 7.4 Hz, 1 H), 7.49 (t, J = 7.8 Hz, 2 H). 13C NMR (100 MHz, CDCl3): δ = 171.6, 133.7, 130.2, 129.2, 128.5.
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