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Synlett 2018; 29(04): 447-451
DOI: 10.1055/s-0036-1590949
DOI: 10.1055/s-0036-1590949
letter
Ammonium Tungstate as an Effective Catalyst for Selective Oxidation of Alcohols to Aldehydes or Ketones with Hydrogen Peroxide under Water – A Synergy of Graphene Oxide
Further Information
Publication History
Received: 17 August 2017
Accepted after revision: 15 October 2017
Publication Date:
17 November 2017 (online)
Abstract
Ammonium tungstate was found to be a facile and efficient catalyst for selective oxidation of alcohols to the corresponding carbonyl compounds with hydrogen peroxide as oxidant. Heterogeneous graphene oxide as acid effectively intensified the transformations and resulted in excellent yields. The use of water as solvent rendered the reactions promising both economically and environmentally.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590949.
- Supporting Information
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- 19 Experimental procedures: GO (0.01 g) was added into water (3 mL) to generate a stable colloidal suspension under mild ultrasonic treatment. Afterwards, the alcohol (2 mmol) and (NH4)5H5[H2(WO4)6] (0.03 mmol, M = 1602) were added. The mixture was stirred for 15 min at room temperature. Subsequently, hydrogen peroxide (30 wt%, 8 mmol) was added dropwise and the mixture was heated to 70 °C until the reaction was complete (monitored by TLC). GO could then be readily separated from the mixtures by centrifugation, and then ethyl acetate was added to the mixture to extract organic constituents. Finally, the organic extracts were concentrated under reduced pressure and purified by column chromatography.Cyclohexanone (Table [2], entry 1): Yield: 0.18 g (93%); colorless liquid. 1H NMR (500 MHz, CDCl3): δ = 2.37 (t, J = 6.7 Hz, 4 H), 2.07–1.82 (m, 4 H), 1.82–1.62 (m, 2 H). 13C NMR (126 MHz, CDCl3): δ = 211.98, 41.92, 26.99, 24.94