Toward efficient palladium-catalyzed allylic C-H alkylation

Chemistry - A European Journal

Volumn 15, Issue 38, 2009, Pages 9632-9636

  Jensen, Thomas ^a   Fristrup, Peter ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

Allylic alkylation; C h activation; Homogeneous catalysis; Palladium

Indexed keywords

ALLYLIC ALKYLATION; C-H ACTIVATION; HOMOGENEOUS CATALYSIS; LEAVING GROUPS; SYNTHETIC EFFICIENCY;

ACTIVATION ANALYSIS; ALKYLATION; CATALYSIS; FLUORINE CONTAINING POLYMERS; PALLADIUM; PALLADIUM COMPOUNDS; REACTION KINETICS;

HYDROCARBONS;

EID: 70450203450     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901935     Document Type: Review

References (35)

1. Metal-Catalyzed Cross-Coupling Reactions (Eds: A. de Meijere, F. Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004.
2. a) H. M. L. Davies, J. R. Manning, Nature 2008, 253-259, 417;
3. b)R. G. Bergman, Nature 2007, 446, 391;
4. c) K. Godula, D. Sames, Science 2006, 312, 67.
5. For reviews of the Tsuji-Trost reaction, see: a) J. Tsuji, Palladium Reagents and Catalysts: New Perspectives for the 21st Century; Wiley, Chichester (UK), 2004, Chapter 4;
6. b) B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921;
7. c) B. M. Trost. J. Org. Chem. 2004, 69, 5813;
8. d) Handbook of Organopalladium Chemistry for Organic Synthesis (Ed: E.-I, Negishi), Wiley-Interscience; New York, 2002.
9. J. Tsuji, H. Takahashi, Tetrahedron Lett. 1965, 6, 4387.
10. B. M. Trost, Ace. Chem. Res. 1980, 13, 385.
11. A. J. Young, M. C. White, J. Am. Chem. Soc. 2008, 130, 14090.
12. S. Lin, C.-X. Song, G.-X. Cai, W.-H. Wang, Z.-J. Shi, J. Am. Chem. Soc. 2008, 130, 12901.
13. a) B. M. Trost, T.J. Fullerton, J. Am. Chem. Soc. 1973, 95, 292;
14. b) B. M. Trost, L. Weber, P. E. Strege, T.J. Fullerton, T.J. Dietsche, J. Am. Chem. Soc. 1978, 100, 3407;
15. c) B. M. Trost, L. Weber, P. E. Strege, T.J. Fullerton, T.J. Dietsche, J. Am. Chem. Soc. 1978, 100, 3416;
16. d) B. M. Trost, L. Weber, P. E. Strege, T. J. Fullerton, T. J. Dietsche, J. Am. Chem. Soc. 1978, 100, 3426.
17. E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318.
18. J. Franzén, J.-E. Bäckvall, J. Am. Chem. Soc. 2003, 125, 6056.
19. J. Piera, K. Närhi, J.-E. Bäckvall, Angew. Chem. 2006, 118, 7068;
20. Angew. Chem. Int. Ed. 2006, 45, 6914.
21. Z. Li, C-J. Li, J. Am. Chem. Soc. 2006, 128, 56.
22. M. S. Chen, M. C White, J. Am. Chem. Soc. 2004, 126, 1346.
23. For examples of palladium(II)-catalyzed formation of allylic acetates from internal alkenes see: a) A. Heumann, M. Reglier, B. Waegell, Angew. Chem. 1982, 94, 397;
24. Angew. Chem. Int. Ed. Engl. 1982, 21, 366;
25. b)A. Heumann, B. Åkermark, Angew. Chem. 1984, 96, 443;
26. Angew. Chem. Int. Ed. Engl. 1984, 23, 453;
27. c) S. Hansson, A. Heumann, T. Rein, B. Åkermark, J. Org. Chem. 1990, 55, 975;
28. d) B. Åkermark, E. M. Larsson, J. D. Oslob, J. Org. Chem. 1994, 59, 5729;
29. e) H. Grennberg, J.-E. Bäckvall, Chem. Eur. J. 1998, 4, 1083.
30. For an example of asymmetric allylic oxidation of cycloalkenes using a bimetallic palladium(II) complex, see: A. K. El-Qisiari, H. A. Qaseer, P. M. Henry, Tetrahedron Lett. 2002, 43, 4229.
31. a) J.-E. Bäckvall, R. B. Hopkins, H. Grennberg, M. M. Mader, A. K. Awasthi, J. Am. Chem. Soc. 1990, 112, 5160;
32. b) K. Itami, A. Palmgren, A. Thorarensen, J.-E. Bäckvall, J. Org. Chem. 1998, 63, 6466.
33. D.J. Covell, M. C. White, Angew. Chem. 2008, 120, 6548;
34. Angew. Chem. Int. Ed. 2008, 47, 6448.
35. R. Mariz, X. Luan, M. Gatti, A. Linden, R. Dorta, J. Am. Chem. Soc. 2008, 130, 2172.