Construction of Palladium-Polypyrrole Catalytic System in the Wacker Oxidation

Synlett

Volumn 1996, Issue 12, 1996, Pages 1213-1214

  Higuchi, Masayoshi ^a   Yamaguchi, Satoshi ^a   Hirao, Toshikazu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542394583     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5722     Document Type: Article

References (10)

1. Durfee, W. S.; Pierpont, C. G. Inorg. Chem. 1993, 32, 493; Hilt, G.; Steckhan, E. J. Chem. Soc., Chem. Commun. 1993, 1706.
2. Durfee, W. S.; Pierpont, C. G. Inorg. Chem. 1993, 32, 493; Hilt, G.; Steckhan, E. J. Chem. Soc., Chem. Commun. 1993, 1706.
3. Hirao, T.; Murakami, T.; Ohno, M.; Ohshiro, Y. Chem. Lett. 1989, 785; 1991, 299; Hirao, T. Rev. Heteroatom Chem. 1994, 11, 207.
4. Hirao, T.; Murakami, T.; Ohno, M.; Ohshiro, Y. Chem. Lett. 1989, 785; 1991, 299; Hirao, T. Rev. Heteroatom Chem. 1994, 11, 207.
5. Hirao, T.; Higuchi, M.; Ikeda, I.; Ohshiro, Y. J. Chem. Soc., Chem. Commun. 1993, 194; Hirao, T.; Higuchi, M.; Ohshiro, Y.; Ikeda, I. Chem. Lett. 1993, 1889.
6. Hirao, T.; Higuchi, M.; Ikeda, I.; Ohshiro, Y. J. Chem. Soc., Chem. Commun. 1993, 194; Hirao, T.; Higuchi, M.; Ohshiro, Y.; Ikeda, I. Chem. Lett. 1993, 1889.
7. Hirao, T.; Higuchi, M.; Hatano, B.; Ikeda, I. Tetrahedron Lett. 1995, 36, 5925.
8. A solution of pyrrole (3.35 g, 50.0 mmol) in 1M HCl (150 mL) was placed in an ice/water bath and cooled. A solution of ammonium peroxodisulfate (2.85 g, 12.5 mmol) in 1M HCl (100 mL) cooled in an ice/water bath was drop wise added to the solution of pyrrole over about 10 min with vigorous stirring. As the polymerization proceeded, the solution turned black and the salt of polypyrrole began to precipitate. After the addition of the ammonium peroxodisulfate solution was completed, the mixture was stirred for additional 2 h. Polypyrrole (0.88 g) was filtered using a Büchner funnel, washed with 1 M HCl (300 mL), acetonitrile (300 mL) and then ether (300 mL), and dried in vacuum at room temperature for 24 h.
9. A typical experiment procedure for the Wacker oxidation reaction of 5-hexen-2-one is as follows. Polypyrrole (40 mg) and palladium(II) acetate (22.4 mg, 0.1 mmol) were dried in vacuum in the reaction vessel. Acetonitrile (2.0 mL) was added under oxygen and stirring was continued at room temperature for 30 min. Then, 5-hexen-2-one (196 mg, 2.0 mmol) and deionized water (540 μL, 30 mmol) were added and stirring was continued at 40 °C for 90 h although the reaction mixture looked heterogeneous. Ether (2 mL) was added to the reaction mixture at room temperature. After stirring for 10 min, the mixture was filtered and concentrated. Yield of 2,5-hexanedione was determined by GLC.
10. Kim, D. Y.; Lee, J. Y.; Moon, D. K.; Kim, C. Y. Synth. Met. 1995, 69, 471.