Evidence for the intermediacy of (η3-allyl)palladium complexes in the palladium-catalyzed acryloxylation of cycloalkenes: Unexpected oxidation of 1,5-cyclooctadiene

European Journal of Organic Chemistry

Volumn , Issue 1, 2000, Pages 219-224

  Jabre Truffert, Sylvaine ^a   Delmas, Anne Marie ^a   Grennberg, Helena ^b   Akermark, Björn ^c   Waegell, Bernard ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

^b UPPSALA UNIVERSITY   (Sweden)

^c ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

1,2 Addition reactions; 1,5 Cyclooctadiene; Acetoxylation; Acryloxylation; Cyclooct 4 enone; Homogeneous catalysis; Palladium

Indexed keywords

CYCLOALKENE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; OXIDATION; REACTION ANALYSIS;

EID: 0033987717     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200001)2000:1<219::aid-ejoc219>3.0.co;2-%23     Document Type: Article

References (27)

1. [1a] H. Grennberg, V. Simon, J. E. Bäckvall, J. Client. Soc., Client Commun. 1994, 265-266.
2. [1b] H. Grennberg, J. E. Bäckvall, Chem. Eur. J. 1998, 4, 1083-1089.
3. [1c] For general references, see J. Tsuji, Palladium Reagents and Catalysts, J. Wiley & Sons, Chichester, 1995.
4. [2a] N. Ferret, L. Mussate-Mathieu, J. P. Zahra, B. Waegell, J. Chem. Soc., Chem. Commun. 1994, 2589-2590.
5. [2b] N. Ferret, L. Mussate-Mathieu, P. Perfetti, J. P. Zahra, B. Waegell, Bull. Soc. Chim. Fr. 1996, 133, 1023-1031.
6. [3a] P. A. Grieco, Synthesis 1975, 67-82.
7. [3b] H. M. R. Hoffmann, J. Rabe, Angew. Chem. Int. Ed. Engl. 1985, 24, 94-110.
8. [3c] N. Petragnani, H. M. C. Ferraz, G. V. Silva, Synthesis 1986, 157-183.
9. S. Jabre-Truffert, V. Lazzeri, B. Waegell, B. Akermark, manuscript in preparation.
10. S. Hanson, A. Heumann, T. Rein, B. Akermark, J. Org. Chem. 1990, 55, 975-984.
11. [6a] P. M. Henry, M. Davies, G. Fergusson, S. Phillips, R. Restivo, J. Chem. Soc., Chem. Commun. 1974, 112-113.
12. [6b] C. B. Anderson, B. J. Burreson, J. Organomet. Chem. 1967, 7, 181-187.
13. A. Gogoll, H. Grennberg, Magn. Reson. 1993, 31, 954-959 and references therein.
14. B. Soderberg, B. Akermark, Y. H. Chen, S. Hall, J. Org. Chem. 1990, 55, 1344-1349.
15. B. Akermark, E. M. Larsson, J. D. Oslob, J. Org. Chem. 1994, 59, 5729-5733.
16. 3-σ)-palladium(II) complex resulting from trans-hydroxy-palladation of 1,5-cyclooctadiene gives cyclooct-4-enone (4): J. K. Stille, D. E. James, J. Organomet. Chem. 1976, 108, 401-408.
17. [11a] P. Barbier, C. Benezra, J. Org. Chem. 1983, 48, 2705-2709.
18. 2, in AcOH.
19. R. G. Schultz, P. R. Rony, J. Catal. 1970, 16, 133-147.
20. 0-benzoquinone complex could be clearly identified by the signal at δ = 5.75, which is characteristic of para-benzoquinone. When acrylic acid was added, a new signal at δ = 6.70 appeared, characteristic of hydroquinone. This gave a clear indication that 1,2-oxypalladation of one double bond had occurred. Other characteristic new signals appeared at δ = 3.12, corresponding to CH-Pd, and at δ = 5.34, corresponding to acrylate CH-O. The 1,2-addition most likely occurs in a trans fashion as the vinylic proton signals of the acrylate are not shifted compared to those of pure acrylic acid. A shift would have indicated coordination of this double bond to the metal center, which would only have been possible if a cis addition had occurred.
21. [14a] L. L. Zakharkin, V. V. Guseva, J. Org. Chem. USSR 1989, 99-102.
22. [14b] A. J. Bloodworth, J. L. Courtneidge, R. J. Curtis, J. Chem. Soc.. Chem. Commun. 1990, 2951-2955.
23. [15a] N. Hanold, H. Meier, Chem. Ber. 1985, 118, 118-209.
24. [15b] M. J. Loots, L. D. Weingarten, R. H. Levin, J .Am. Chem. Soc. 1976, 98, 4571-4577.
25. [16a] L. Mussate-Mathieu, S. Truffert-Jabre, J. P. Zahra, B. Waegell, manuscript in preparation.
26. [16b] L. Mussate-Mathieu, Thèse de Doctorat en Sciences, Université d'Aix-Marseille III, March 1994.
27. R. Deghenghi, Ch. R. Engel, J. Am. Chem. Soc. 1960, 82, 3201-3209.