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Synlett 2017; 28(05): 607-610
DOI: 10.1055/s-0036-1588656
DOI: 10.1055/s-0036-1588656
letter
Selective Oxidation of Styrene Derivatives to Ketones over Palladium(0)/Carbon with Hydrogen Peroxide as the Sole Oxidant
Further Information
Publication History
Received: 08 September 2016
Accepted after revision: 29 October 2016
Publication Date:
18 November 2016 (online)
![](https://www.thieme-connect.de/media/synlett/201705/lookinside/thumbnails/st-2016-w0599-l_10-1055_s-0036-1588656-1.jpg)
Abstract
Pd0/C catalyst exhibited excellent catalytic activity in the Wacker oxidation of styrene derivatives to corresponding ketones with hydrogen peroxide as a clean oxidant. Compared with the conventional Wacker system, the newly developed method offers a cost-efficient and environmentally friendly option without the use of a copper salt as a co-catalyst.
Key words
Wacker oxidation - palladium catalysis - heterogeneous catalysis - hydrogen peroxide - styrenes - ketonesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588656.
- Supporting Information
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- 21 Wacker Oxidation of Olefins; General Procedure 5 wt% Pd0/C (0.05 mmol) and 70 wt% H2SO4 (0.2 mmol) were added to a solution of the appropriate styrene (1 mmol) in MeCN (5 mL), and the mixture was stirred for about 15 min at r.t. Then, 30 wt% H2O2 (6 mmol) was added dropwise, and the mixture was heated at 65 °C until the reaction was complete (TLC). The Pd0/C was removed by centrifugation and the remaining mixture was partitioned between H2O and EtOAc. The layers were separated, and the organic layer was washed with H2O, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography. Acetophenone (Table 2, Entry 16) Light-yellow liquid; yield: 1.03 g (90%). 1H NMR (300 MHz, CDCl3): δ = 7.96 (d, J = 7.1 Hz, 2 H), 7.57 (t, J = 7.3 Hz, 1 H), 7.47 (t, J = 7.4 Hz, 2 H), 2.61 (s, 3 H). 13C NMR (75 MHz, CDCl3): δ = 198.1, 136.9, 133.0, 128.4, 128.2, 26.5.