Intra/intermolecular direct allylic alkylation via Pd(II)-catalyzed allylic C-H activation

Journal of the American Chemical Society

Volumn 130, Issue 39, 2008, Pages 12901-12903

  Lin, Song ^a   Song, Chun Xiao ^a   Cai, Gui Xin ^a   Wang, Wen Hua ^a   Shi, Zhang Jie ^a,b  

^a PEKING UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALKYLATION; C-H ACTIVATION; C-H BOND; CHEMICAL EQUATIONS; CYCLIC COMPOUNDS; DIRECT ALKYLATION;

ACTIVATION ANALYSIS; ALKYLATION; HYDROCARBONS; PALLADIUM;

PALLADIUM COMPOUNDS;

EID: 67650292726     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja803452p     Document Type: Article

References (51)

1. For reviews of Tsuji-Trost reactions, see: (a) Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century; John Wiley & Sons, Ltd.: Chichester, U.K., 2004; Chapter 4, p 431.
2. (b) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
3. (c) Negishi, E.-I., Ed. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002.
4. For representative examples of the application of allylic alkylation in organic synthesis, see: (a) Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2315.
5. (b) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1983, 24, 4713.
6. (c) Huang, Y.; Lu, X. Tetrahedron Lett. 1988, 29, 5663.
7. (d) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482.
8. (e) Dai, L.; Tu, T.; You, S.; Deng, W.; Hou, X. Acc. Chem. Res. 2003, 36, 659.
9. (f) Alexakis, A.; Malan, C.; Lea, L.; Tissot-Croset, K.; Polet, D.; Falciola, C. Chimia 2006, 60, 124.
10. (g) Kammerer, C.; Prestat, G.; Gaillard, T.; Madec, D.; Poli, G. Org. Lett. 2008, 10, 405.
11. (h) Kacprzynski, M. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 10676.
12. (a) Kazmaier, U.; Pohlman, M. In Metal-Catalyzed Cross-Coupling Reactions; 2nd ed.; De Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 9, p 531.
13. (b) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140.
14. For reviews of allylic C-H bond activation, see: Dyker, G., Ed. Handbook of C-H Transformations; Wiley-VCH: Weinheim, Germany, 2005; Chapter 4, p 402 and references therein.
15. (a) Trost, B. M.; Fullerton, T. J. J. Am. Chem. Soc. 1973, 95, 292.
16. (b) Trost, B. M.; Metzner, P. J. J. Am. Chem. Soc. 1980, 102, 3572.
17. (c) Trost, B. M.; Strege, P. E.; Weber, L.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3407.
18. 3 C-H bonds, see: (a) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 56.
19. (b) Li, Z.; Bohle, D. S.; Li, C.-J. Proc. Natl. Acad. Sci.U.S.A. 2006, 103, 8928.
20. (c) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810.
21. (d) Li, Z.; Cao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2007, 46, 6505.
22. (e) Zhang, Y.; Li, C.-J. Angew. Chem., Int. Ed. 2006, 45, 1949.
23. (f) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968.
24. (g) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 3672.
25. (h) Zhang, Y.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 4242.
26. (i) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
27. (j) Dwight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. Org. Lett. 2007, 9, 3137.
28. (a) Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2008, 130, 3316.
29. (b) Fraunhoffer, K. J.; White, M. C. J. Am. Chem. Soc. 2007, 129, 7274.
30. (c) Delcamp, J. H.; White, M. C. J. Am. Chem. Soc. 2006, 128, 15076.
31. (d) Fraunhoffer, K. J.; Prabagaran, N.; Sirois, L. E.; White, M. C. J. Am. Chem. Soc. 2006, 128, 9032.
32. (e) Chen, M. S.; Prabagaran, N.; Labenz, N. A.; White, M. C. J. Am. Chem. Soc. 2005, 127, 6970.
33. (f) Fraunhoffer, K. J.; Bachovchin, D. A.; White, M. C. Org. Lett. 2005, 7, 223.
34. (g) Chen, M. S.; White, M. C. J. Am. Chem. Soc. 2004, 126, 1346.
35. Liu, G.; Yin, G.; Wu, L. Angew. Chem., Int. Ed. 2008, 47, 4733.
36. Beesley, R. M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc. 1915, 107, 1080.
37. (a) Pei, T.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 648.
38. (b) Smidt, J.; Hafner, W.; Jira, R.; Sedlmeier, J.; Sieber, R.; Ruttinger, R.; Kojer, H. Angew. Chem. 1959, 71, 176.
39. Cheng, D.; Bao, W. Adv. Synth. Catal. 2008, 350, 1263.
40. For representative reports on BQ promoted oxidative systems, see: (a) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400, and references therein.
41. (b) An, Z.; Pan, X.; Liu, X.; Han, X.; Bao, X. J. Am. Chem. Soc. 2006, 128, 16028.
42. (c) Uozumi, Y.; Kato, K.; Hayashi, T. J. Org. Chem. 1998, 63, 5071.
43. (d) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620.
44. For representative example of Pd complexes with chiral sulfoxide ligands, see: Pettinari, C.; Pellei, M.; Cavicchio, G.; Crucianelli, M.; Panzeri, W.; Colapietro, M.; Cassetta, A. Organometallics 1999, 18, 555.
45. For reviews of ligand-controlled stereoselective allylation, see: (a) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
46. (b) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
47. (c) Lübbers, T. In Houben-Weyl Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Rulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, Germany, 1996; p 2429.
48. For representative examples using chiral ligands in allylic alkylation, see: (a) Deng, W.; You, S.; Hou, X.; Dai, L.; Yu, Y.; Xia, W.; Sun, J. J. Am. Chem. Soc. 2001, 123, 6508.
49. (b) Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. 1995, 34, 2386.
50. (c) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031.
51. (d) Sawamura, M.; Nagata, H.; Sakamoto, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 2586.