Synlett 2017; 28(05): 607-610
DOI: 10.1055/s-0036-1588656
letter
© Georg Thieme Verlag Stuttgart · New York

Selective Oxidation of Styrene Derivatives to Ketones over Palladium(0)/Carbon with Hydrogen Peroxide as the Sole Oxidant

Xiaomeng Xia
a   School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, P. R. of China
,
Xi Gao
a   School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, P. R. of China
,
Junhui Xu
a   School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, P. R. of China
,
Chuanfeng Hu
a   School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, P. R. of China
,
Xinhua Peng*
a   School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, P. R. of China
b   Lianyungang Institute, Nanjing University of Science and Technology, Lianyungang, 222006, P. R. of China   eMail: xhpeng@mail.njust.edu.cn
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Publikationsverlauf

Received: 08. September 2016

Accepted after revision: 29. Oktober 2016

Publikationsdatum:
18. November 2016 (online)


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.

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.