Wacker-type oxidation of internal olefins using a PdCl2/N,N- dimethylacetamide catalyst system under copper-free reaction conditions

Angewandte Chemie - International Edition

Volumn 49, Issue 7, 2010, Pages 1238-1240

  Mitsudome, Takato ^a   Mizumoto, Keiichi ^a   Mizugaki, Tomoo ^a   Jitsukawa, Koichiro ^a   Kaneda, Kiyotomi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Aerobic oxidation; Alkenes; Homogeneous catalysis; Oxidation; Palladium

Indexed keywords

AEROBIC OXIDATIONS; ALKENES; CATALYST SYSTEM; HOMOGENEOUS CATALYSIS; N ,N-DIMETHYLACETAMIDE; REACTION CONDITIONS; WACKER-TYPE OXIDATION;

CATALYSIS; CATALYSTS; COPPER COMPOUNDS; OLEFINS; PALLADIUM; REACTION KINETICS;

INTERNAL OXIDATION;

EID: 76349094294     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200905184     Document Type: Article

References (30)

1. H. Siegel, M. Eggersdorfer, Ullmann's Encyclopedia of Industrial Chemistry, Vol.18, 6th ed. (Eds.: M. Bohnet), VCH, Weinheim, 2003, p. 739.
2. a) J. Smidt, W. Hahner, R. Jima, J. Sedlmeier, R. Sieber, R. Rüttinger, K. Kojer, Angew. Chem. 1959, 71, 176;
3. b) J. Smidt, W. Hafner, R. Jira, R. Sieber, J. Sedlmeier, A. Sabel, Angew. Chem. 1962, 74, 93;
4. Angew. Chem. Int. Ed. Engl. 1962, 1, 80;
5. c) R. Jira, Angew. Chem. 2009, 121, 9196;
6. Angew. Chem. Int. Ed. 2009, 45, 9034.
7. J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester, 2004.
8. B. Åkermark, K. Zetterberg, Handbook of Organopalladium Chemistry for Organic Synthesis, Vol.2 (Ed.: E. Negishi), Wiley, New York, 2002, p. 1875.
9. P. M. Henry, Handbook of Organopalladium Chemistry for Organic Synthesis, Vol.2 (Ed.: E. Negishi), Wiley, New York, 2002, p. 2119.
10. W. H. Clement, C. M. Selwitz, J. Org. Chem. 1964, 29, 241.
11. J. Tsuji, Synthesis 1984, 369.
12. J. M. Tackas, X. T. Jiang, Curr. Org. Chem. 2003, 7, 369.
13. H. Alper, K. Januszkiewicz, D. J. H. Smith, Tetrahedron Lett. 1985, 26, 2263.
14. D. G. Miller, D. D. M. Wayner, J. Org. Chem. 1990, 55, 2924.
15. D. G. Miller, D. D. M. Wayner, Can. J. Chem. 1992, 70, 2485.
16. M. Higuchi, S. Yamaguchi, T. Hirao, Synlett 1996, 1213.
17. G.-J. ten Brink, I. W. C. E. Arends, G. Papadogianakis, R. A. Sheldon, Chem. Commun. 1998, 2359.
18. T. Mitsudome, T. Umetani, N. Nosaka, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, Angew. Chem. 2006, 118, 495;
19. Angew. Chem. Int. Ed. 2006, 45, 481.
20. C. N. Cornell, M. S. Sigman, Org. Lett. 2006, 5, 4117.
21. T. Nishimura, N. Kakiuchi, T. Onoue, K. Ohe, S. Uemura, J. Chem. Soc. Perkin Trans. 1 2000, 1915.
22. The high selectivity for β-functionalized ketones might be due to a precoordination of a functional group of the olefin with a palladium prior to the attack of water to the olefin. See reference [18].
23. J. A. Wright, M. J. Gaunt, J. B. Spencer, Chem. Eur. J. 2006, 12, 949.
24. J. Tsuji, H. Nagashima, H. Nemoto, Org. Synth. 1984, 62, 9.
25. 2 was increased. See Figure 1S in the Supporting Information.
26. J. A. Keith, R. J. Niesen, J. Oxgaard, W. A. Goddard, J. Am. Chem. Soc. 2007, 129, 12342.
27. T. Hosokawa, T. Nomura, S.-I. Murahashi, J. Organomet. Chem. 1998, 551, 387.
28. The exact mechanism of this Wacker-type reaction is not yet known. However, evidence indicates these reactions are dependent upon experimental conditions (see reference [5]). Thus, it is not surprising that the observed rate law for this reaction, which does not utilize copper salts, is different from that of the industrial process, which does utilize copper salts (see the Supporting Information).
29. 2/DMA complexes have been studied in the following papers: a) M. Donati, D. Morelli, F. Conti, R. Ugo, Chim. Ind. 1968, 50, 231;
30. b) S. N. Kurskov, V. I. Labunskaya, E. V. Trushina, Koord. Khim. 1990, 16, 1671.