Asymmetrie synthesis of functionalized 1,3-diphosphines via chiral palladium complex promoted hydrophosphination of activated Olefins

Inorganic Chemistry

Volumn 49, Issue 3, 2010, Pages 989-996

  Yuan, Mingjun ^a   Zhang, Na ^a   Pullarkat, Sumod A ^a   Li, Yongxin ^a   Liu, Fengli ^a   Pham, Phuong Tu ^a   Leung, Pak Hing ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ORGANOMETALLIC COMPOUND; PALLADIUM; PHOSPHINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKENES; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHOSPHINES; STEREOISOMERISM;

EID: 75649094148     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic9018053     Document Type: Article

References (52)

1. (a) Baratta, W.; Herdtweck, E.; Siega, K.; Toniutti, M.; Rigo, P. Orgunometallics 2005, 24, 1660.
2. (b) Burke, B. J.; Overman, L. E. J. Am. Chem. Soc. 2004, 126, 16820.
3. Portscheller, J. L.; Lilley, S. E.; Malinakova, H. C. Organometallics 2003, 22, 2961.
4. Homanen, P.; Persson, R.; Haukka, M.; Pakkanen, T. A.; Nordlander, E. Organometallics 2000, 19, 5568.
5. (e) Bergamini, P.; Costa, E.; Orpen, A. G.; Pringle, P. G.; Smith, M. B. Organometallics 1995, 14, 3178.
6. (f) Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayashi, K.; Kohsuke, A. Chem. Commun. 2004, 98.
7. (g) Blanc, D.; Henry, J.-C.; Ratovelomanana-Vidal, V.; Gent, J.-P. Tetraedron Lett. 1997, 38, 6603.
8. (h) Diéguez, M.; Pereira, M. M.; Masdeu-Bultó, A. M.; Claver, C.; Bayón, J. C. J. Mol. Catal. A: Chem. 1999, 143, 111.
9. (a) MacNeil, P. A.; Roberts, N. K.; Bosnich, B. J. Am. Chem. Soc. 1981, 103, 2273.
10. (b) Bakos, J.; Tóth, I.; Heil, B.; Markó, L. J. Orgunomet. Chem. 1985, 279, 23.
11. Halterman, R. L.; Nimmons, H. L. Organometallics 1990, 9, 273.
12. Brunner, H.; Terfort, A. Tetrahedron: Asymmetry 1995, 6, 919.
13. (e) Dubrovina, N. V.; Tararov, V. I.; Monsees, A.; Kadyrov, R.; Fischer, C.; Bömer, A. Terahedron: Asymmetry 2003, 14, 2739.
14. (f) Herseczki, Z.; Gergely, I.; Hegedüs, C.; Szöllösy, Á.; Bakos, J. Tetrahedron: Asymmetry 2004, 15, 1673.
15. (g) Fries, G.; Wolf, J.; Ilg, K.; Walfort, B.; Stalke, D.; Werner, H. Dalton Trans. 2004, 1873.
16. (h) Dubrovina, N. V.; Tararov, V. I.; Monsees, A.; Spannenberg, A.; Kostasc, I. D.; Bömer, A. Tetrahedron: Asymmetry 2005, 16, 3640.
17. (a) Farkas, E.; Rollár, L.;Moret, M.; Sironi, A. Organometallics 1996, 15, 1345.
18. (b) Steffen, W. L.; Palenik, G. J. Inorg. Chem. 1976, 15, 2432.
19. Jánosi, L.; Kollár, L.; Macchi, P.; Sironi, A. J. Organomet. Chem. 2006, 691, 2846.
20. Bakos, J.; Tóth, I.; Heil, B.; Szalontai, G.; Párká nyi, L.; Fülöp, V. J. Organomet. Chem. 1989, 370, 263.
21. (a) Wiese, B.; Knühl, G.; Flubacher, D.; Prieß, J. W.; Ulriksen, B.; Brödner, K.; Helmchen, G. Eur. J. Org. Chem. 2005, 3246.
22. (b) Enders, D.; Saint-Dizier, A.; Lannou, M.-I.; Lenzen, A. Eur. J. Org. Chem. 2006, 29.
23. Imamoto, T.; Kusumoto, T.; Suzuki, N.; Sato, K. J. Am. Chem. Soc. 1985, 107, 5301.
24. Sadow, A. D.; Togni, A. J. Am. Chem. Soc. 2005, 127, 17012.
25. (e) Carlone, A.; Bartoli, G.; Bosco, M.; Sambri, L.; Melchiorre, P. Angew. Chem., Int. Ed. 2007, 46, 4504.
26. (f) Léautey, M.; Géraldine, C. D.; Jubault, P.; Pannecoucke, X.; Quirion, J. C. J. Org. Chem. 2001, 66, 5566.
27. (g) Minami, T.; Okada, Y.; Otaguro, T.; Tawaraya, S.; Furuichi, T.; Okauchi, T. Tetrahedron: Asymmetry 1995, 6, 2469.
28. (h) Bourumeau, K.; Gaumont, A. C.; Denis, J. M. Tetrahedron Lett. 1997, 38, 1923.
29. For hydrophosphination reactions, see: (a) Pullarkat, S. A.; Ding, Y.; Li, Y.; Tan, G. K.; Leung, P. H. Inorg. Chem. 2006, 45, 7455.
30. (b) Tang, L. L.; Zhang, Y.; Luo, D.; Li, Y.; Mok, K. F.; Yeo, W. C.; Leung, P. H. Tetrahedron Lett. 2007, 48, 33.
31. Zhang, Y.; Tang, L.; Ding, Y.; Chua, J.-H.; Li, Y; Yuan, M.; Leung, P. H. Tetrahedron Lett. 2008, 49, 1762.
32. (d) Yuan, M.; Pullarkat, S. A.; Ma, M.; Zhang, Y.; Huang, Y.; Li, Y.; Goel, A.; Leung, P. H. Organometallics 2009, 28, 780.
33. (e) Zhang, Y.; Pullarkat, S. A.; Li, Y.; Leung, P. H. Inorg. Chem. 2009, 48, 5535.
34. (f) Liu, F.; Pullarkat, S. A.; Li, Y.; Chen, S.; Yuan, M.; Lee, Z. Y.; Leung, P. H. Organometallics 2009, 28, 3941.
35. For Diels- Alder reactions, see: (a) Leung, P. H. Acc. Chem. Res. 2004, 37, 169.
36. (b) Yeo, W. C.; Chen, S.; Tan, G. -K.; Leung, P. H. Organomet. Chem. 2007, 692, 2539.
37. Yuan, M.; Pullarkat, S. A.; Yeong, C. H.; Li, Y.; Krishnan, D.; Leung, P. H. Dalton Trans. 2009, 3668.
38. Ma, M.; Pullarkat, S. A.; Yuan, M.; Zhang, N.; Li, Y.; Leung, P. H. Organometallics 2009, 28, 4886.
39. (e) Pullarkat, S. A.; Cheow, Y. L.; Li, Y.; Leung, P. H. Eur. J. Inorg. Chem. 2009, 2375.
40. (a) Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244.
41. (b) Moiseev, D. V.; Patrick, B. O.; James, B. R. Inorg. Chem. 2007, 46, 11467.
42. (8)(a) Lutz, C.; Graf, C. D.; Knochel, P. Tetrahedron 1998, 54, 10317.
43. (b) Vaughn, G. D.; Gladysz, J. A. J. Am. Chem. SOC. 1986, 108, 1473.
44. The interconversion between regioisomers 5 and 6 is very fast especially in coordinating solvent, such as acetonitrile, compared with the similar 1,2-diphosphine palladium complexes (see ref 5). The equilibrium can be attained within 2 h at room temperature.
45. (a) Chikkali, S.; Gudat, D. Eur. J. Inorg. Chem. 2006, 3005.
46. (b) Kolodiazhnyi, O. I.; Guliaiko, I. V.; Kolodiazhna, A. O. Tetrahedron Lett. 2004, 45, 6955.
47. Bourumeau, K.; Gaumont, A.-C.; Denis, J.-M. J. Organomet. Chem. 1997, 529, 205.
48. Suzuki, K.; Hashimoto, T.; Maeta, H.; Matsumoto, T. Synlett 1992, 125.
49. (e) Epstein, M.; Buckler, S. A. Tetrahedron 1962, 18, 1231.
50. (a) Hockless, D. C. R.; Gugger, P. A.; Leung, P. H.; Mayadunne, R. C.; Pabel, M.; Wild, S. B. Tetrahedron 1997, 53, 4083.
51. (b) Allen, D. G.; McLaughlin, G. M.; Robertson, G. B.; Steffen, W. L.; Salem, G.; Wild, S. B. Inorg. Chem. 1982, 21, 1007.
52. Chooi, S. Y. M.; Siah, S. Y.; Leung, P. H.; Mok, K. F. Inorg. Chem. 1993, 32, 4812.