Novel synthesis of chiral 1,3-diphosphines via palladium template promoted hydrophosphination and functional group transformation reactions

Organometallics

Volumn 29, Issue 16, 2010, Pages 3582-3588

  Yuan, Mingjun ^a   Pullarkat, Sumod A ^a   Li, Yongxin ^a   Lee, Zhi Yi ^a   Leung, Pak Hing ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; CHIRAL AUXILIARIES; DIPHENYLPHOSPHINE; DIPHOSPHINES; FUNCTIONAL GROUP TRANSFORMATIONS; FUNCTIONALIZED; GOOD YIELD; HIGH YIELD; HYDROPHOSPHINATION; HYDROXYL FUNCTIONALITY; ONE POT PROCESS; PALLADIUM COMPLEXES; POTASSIUM CYANIDES;

CYANIDES; FUNCTIONAL GROUPS; NAPHTHALENE; PALLADIUM; PALLADIUM COMPOUNDS; POTASSIUM; PROPANE; SUBSTRATES; X RAY CRYSTALLOGRAPHY;

COORDINATION REACTIONS;

EID: 77955682109     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100505w     Document Type: Article

References (77)

1. Knowles, W. S. Acc. Chem. Res. 1983, 16, 106
2. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345
3. Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375
4. Ohff, M.; Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1998, 1391
5. Hayashi, T. Acc. Chem. Res. 2000, 33, 354
6. Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029
7. Colacot, T. J. Chem. Rev. 2003, 103, 3101
8. Crépy, K. V. L.; Imamoto, T. Top. Curr. Chem. 2003, 229, 1-40.
9. Li, Y.-M.; Kwong, F.-Y.; Yu, W.-Y.; Chan, A. S. C. Coord. Chem. Rev. 2007, 251, 2119
10. Glueck, D. S. Chem.-Eur. J. 2008, 14, 7108
11. Xie, J.-H.; Zhou, Q.-L. Acc. Chem. Res. 2008, 41, 581
12. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857
13. Börner, A. Eur. J. Inorg. Chem. 2001, 327
14. Theil, A.; Hitce, J.; Retailleau, P.; Marinetti, A. Eur. J. Org. Chem. 2006, 154
15. Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727
16. Landis, C. R.; Sawyer, R. A.; Somsook, E. Organometallics 2000, 19, 994
17. Blaser, H.-U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103
18. For hydrophosphination reactions, see: Pullarkat, S. A.; Ding, Y.; Li, Y.; Tan, G. K.; Leung, P. H. Inorg. Chem. 2006, 45, 7455
19. Tang, L. L.; Zhang, Y.; Luo, D.; Li, Y.; Mok, K. F.; Yeo, W. C.; Leung, P. H. Tetrahedron Lett. 2007, 48, 33
20. Zhang, Y.; Tang, L.; Ding, Y.; Chua, J.-H.; Li, Y.; Yuan, M.; Leung, P. H. Tetrahedron Lett. 2008, 49, 1762
21. Yuan, M.; Pullarkat, S. A.; Ma, M.; Zhang, Y.; Huang, Y.; Li, Y.; Goel, A.; Leung, P. H. Organometallics 2009, 28, 780
22. Zhang, Y.; Pullarkat, S. A.; Li, Y.; Leung, P. H. Inorg. Chem. 2009, 48, 5535
23. Liu, F.; Pullarkat, S. A.; Li, Y.; Chen, S.; Yuan, M.; Lee, Z. Y.; Leung, P. H. Organometallics 2009, 28, 3941
24. Yuan, M.; Zhang, N.; Pullarkat, S. A.; Li, Y.; Liu, F.; Pham, P.-T.; Leung, P. H. Inorg. Chem. 2010, 49, 989
25. Huang, Y.; Pullarkat, S. A.; Yuan, M.; Ding, Y.; Li, Y.; Leung, P. H. Organometallics 2010, 29, 536
26. For Diels-Alder reactions, see: Leung, P. H. Acc. Chem. Res. 2004, 37, 169, and references therein.
27. Yeo, W. C.; Chen, S.; Tan, G.-K.; Leung, P. H. J. Organomet. Chem. 2007, 692, 2539
28. Yuan, M.; Pullarkat, S. A.; Yeong, C. H.; Li, Y.; Krishnan, D.; Leung, P. H. Dalton Trans. 2009, 3668
29. Ma, M.; Pullarkat, S. A.; Yuan, M.; Zhang, N.; Li, Y.; Leung, P. H. Organometallics 2009, 28, 4886
30. Pullarkat, S. A.; Cheow, Y. L.; Li, Y.; Leung, P. H. Eur. J. Inorg. Chem. 2009, 2375
31. Farkas, E.; Kollár, L.; Moret, M.; Sironi, A. Organometallics 1996, 15, 1345
32. Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayashi, K.; Aikawa, K. Tetrahedron 2004, 60, 4475
33. Jánosi, L.; Kollár, L.; Macchi, P.; Sironi, A. J. Organomet. Chem. 2006, 691, 2846
34. Bakos, J.; Tóth, I.; Heil, B.; Szalontai, G.; Párká nyi, L.; Fülöp, V. J. Organomet. Chem. 1989, 370, 263
35. Steffen, W. L.; Palenik, G. J. Inorg. Chem. 1976, 15, 2432
36. Berning, D. E.; Noll, B. C.; DuBois, D. L. J. Am. Chem. Soc. 1999, 121, 11432
37. Keim, W.; Kraneburg, P.; Dahmen, G.; Deckers, G.; Englert, U.; Linn, K.; Spaniol, T. P.; Raabe, G.; Krüger, C. Organometallics 1994, 13, 3085
38. Dodge, T.; Curtis, M. A.; Russell, J. M.; Sabat, M.; Finn, M. G.; Grimes, R. N. J. Am. Chem. Soc. 2000, 122, 10573
39. Yang, J. Y.; Bullock, R. M.; Shaw, W. J.; Twamley, B.; Fraze, K.; DuBois, M. R.; DuBois, D. L. J. Am. Chem. Soc. 2009, 131, 5935
40. Suzuki, T.; Tsuji, N.; Kashiwabara, K.; Tatsumi, K. Inorg. Chem. 2000, 39, 3938
41. Suzuki, T.; Kashiwabara, K.; Usami, T.; Imamura, T.; Kiki, M.; Fujita, J.; Kaizaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 1055
42. MacNeil, P. A.; Roberts, N. K.; Bosnich, B. J. Am. Chem. Soc. 1981, 103, 2273
43. Bakos, J.; Tóth, I.; Heil, B.; Markó, L. J. Organomet. Chem. 1985, 279, 23
44. Halterman, R. L.; Nimmons, H. L. Organometallics 1990, 9, 273
45. Brunner, H.; Terfort, A. Tetrahedron: Asymmetry 1995, 6, 919
46. Dubrovina, N. V.; Tararov, V. I.; Monsees, A.; Kadyrov, R.; Fischer, C.; Börner, A. Tetrahedron: Asymmetry 2003, 14, 2739
47. Herseczki, Z.; Gergely, I.; Hegedüs, C.; Szöllosy, Á.; Bakos, J. Tetrahedron: Asymmetry 2004, 15, 1673
48. Fries, G.; Wolf, J.; Ilg, K.; Walfort, B.; Stalke, D.; Werner, H. Dalton Trans. 2004, 1873
49. Dubrovina, N. V.; Tararov, V. I.; Monsees, A.; Spannenberg, A.; Kostasc, I. D.; Börner, A. Tetrahedron: Asymmetry 2005, 16, 3640
50. Baillie, C.; Xiao, J. Curr. Org. Chem. 2003, 7, 477
51. Odinets, I. L.; Vinogradova, N. M.; Matveeva, E. V.; Mastryukova, T. A. Curr. Org. Chem. 2005, 9, 1899
52. Wiese, B.; Knühl, G.; Flubacher, D.; Priess, J. W.; Ulriksen, B.; Brödner, K.; Helmchen, G. Eur. J. Org. Chem. 2005, 3246
53. Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039
54. Sadow, A. D.; Togni, A. J. Am. Chem. Soc. 2005, 127, 17012
55. Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S. Organometallics 2000, 19, 950
56. Gourdel, Y.; Pellon, P.; Toupet, L.; Corre, M. L. Tetrahedron Lett. 1994, 35, 1197
57. Ando, K.; Suzuki, Y. Tetrahedron 1995, 51, 2325
58. Li, Y.; Li, Z.; Li, F.; Wang, Q.; Tao, F. Tetrahedron Lett. 2005, 46, 6159
59. Blinn, D. A.; Button, R. S.; Farazi, V.; Neeb, M. K.; Tapley, C. L.; Trehearne, T. E.; West, S. D.; Kruger, T. L.; Storhoff, B. N. J. Organomet. Chem. 1990, 393, 143
60. Kawasaki, S.; Nakamura, A.; Toyota, K.; Yoshifuji, M. Bull. Chem. Soc. Jpn. 2005, 78, 1110
61. Marvin, C. C.; Voight, E. A.; Suh, J. M.; Paradise, C. L.; Burke, S. D. J. Org. Chem. 2008, 73, 8452
62. Kromann, H.; Larsen, M.; Boesen, T.; Schønning, K.; Nielsen, S. F. Eur. J. Med. Chem. 2004, 39, 993
63. Papahatjis, D. P.; Nahmias, V. R.; Nikas, S. P.; Andreou, T.; Alapafuja, S. O.; Tsotinis, A.; Guo, J.; Fan, P.; Makriyannis, A. J. Med. Chem. 2007, 50, 4048
64. Magatti, C. V.; Kaminski, J. J.; Rothberg, I. J. Org. Chem. 1991, 56, 3102
65. Newkome, G. R.; Arai, S.; Fronczek, F. R.; Moorefield, C. N.; Lin, X.; Weis, C. D. J. Org. Chem. 1993, 58, 898
66. Ravindranathan, M.; Kalyanam, N.; Sivaram, S. J. Org. Chem. 1982, 47, 4812
67. Frejd, T.; Klingstedt, T. Synthesis 1987, 40
68. Badorrey, R.; Cativiela, C.; Díaz-de-Villegas, M. D.; Gálvez, J. A.; Gil, A. Tetrahedron: Asymmetry 2003, 14, 2209
69. Fitz, M.; Forró, E.; Vigóczki, E.; Lázár, L.; Fülöp, F. Tetrahedron: Asymmetry 2008, 19, 1114
70. PP = 54.9 Hz). However, the minor regioisomers 7a and 8a cannot be isolated at this stage.
71. Without addition of NaI, the reaction will yield the dichloro palladium complex. However, the solubility of the dichloro analogue of 10a is too poor for characterization.
72. The absolute configurations of the chiral diiodo palladium complex 9a and the regioisomers 5a and 6a were revealed by the following functional group transformation reactions.
73. Hockless, D. C. R.; Gugger, P. A.; Leung, P. H.; Mayadunne, R. C.; Pabel, M.; Wild, S. B. Tetrahedron 1997, 53, 4083
74. Allen, D. G.; McLaughlin, G. M.; Robertson, G. B.; Steffen, W. L.; Salem, G.; Wild, S. B. Inorg. Chem. 1982, 21, 1007
75. Chooi, S. Y. M.; Siah, S. Y.; Leung, P. H.; Mok, K. F. Inorg. Chem. 1993, 32, 4812
76. Burling, S.; Paine, B. M.; Nama, D.; Brown, V. S.; Mahon, M. F.; Prior, T. J.; Pregosin, P. S.; Whittlesey, M. K.; Williams, J. M. J. J. Am. Chem. Soc. 2007, 129, 1987
77. Kiddle, J. J. Tetrahedron Lett. 2000, 41, 1339