Palladacycle mediated synthesis of cyano-functionalized chiral 1,2-diphosphine and subsequent functional group transformations

Journal of Organometallic Chemistry

Volumn 696, Issue 4, 2011, Pages 905-912

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

^a Nanyang Technological University   (Singapore)

Author keywords

Allylic phosphine; Asymmetric hydrophosphination; Chiral diphosphine; Palladacycle

Indexed keywords

ABSOLUTE CONFIGURATION; ALLYLIC PHOSPHINE; CHIRAL AUXILIARIES; CHIRAL DIPHOSPHINE; COORDINATION PROPERTIES; DIASTEREOSELECTIVE; DIPHOSPHINES; FUNCTIONAL GROUP TRANSFORMATIONS; FUNCTIONALIZED; HIGH YIELD; HYDROPHOSPHINATION; ONE POT PROCESS; ORGANIC TRANSFORMATIONS; PALLADACYCLES; PALLADIUM COMPLEXES; POTASSIUM CYANIDES; SINGLE CRYSTAL X-RAY CRYSTALLOGRAPHY; SUBSTITUTED PRODUCTS;

CYANIDES; ETHANE; FUNCTIONAL GROUPS; NAPHTHALENE; PALLADIUM COMPOUNDS; PHOSPHORUS COMPOUNDS; POTASSIUM; SINGLE CRYSTALS; STEREOSELECTIVITY; X RAY CRYSTALLOGRAPHY;

COORDINATION REACTIONS;

EID: 79551502536     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.10.029     Document Type: Article

References (59)

1. P.R. Auburn, P.B. Mackenzie, and B. Bosnich J. Am. Chem. Soc. 107 1985 2033 2046
2. M.D. Fryzuk, and B. Bosnich J. Am. Chem. Soc. 99 1977 6262 6267
3. P. Mauleón, and J.C. Carretero Org. Lett. 6 2004 3195 3198
4. P. Mauleón, and J.C. Carretero Chem. Commun. 2005 4961 4963
5. P. Mauleón, I. Alonso, M.R. Rivero, and J.C. Carretero J. Org. Chem. 72 2007 9924 9935
6. T. Nishikata, Y. Yamamoto, and N. Miyaura Adv. Synth. Catal. 349 2007 1759 1764
7. T. Nishikata, S. Kiyomura, Y. Yamamoto, and N. Miyaura Synlett 2008 2487 2490
8. T. Nishikata, Y. Yamamoto, and N. Miyaura Chem. Lett. 36 2007 1442 1443
9. K. Akiyama, K. Wakabayashi, and K. Mikami Adv. Synth. Catal. 347 2005 1569 1575
10. M.D. Fryzuk, and B. Bosnich J. Am. Chem. Soc. 100 1978 5491 5494
11. D. Carmona, M.P. Lamata, F. Viguri, R. Rodríguez, F.J. Lahoz, and L.A. Oro Chem. - Eur. J. 13 2007 9746 9756
12. D. Carmona, C. Cativiela, R. García-Correas, F.J. Lahoz, M.P. Lamata, J.A. López, M.P. López-Ram de Víu, L.A. Oro, E.S. José, and F. Viguri Chem. Commun. 1996 1247 1248
13. Y. Matsuo, Y. Mitani, Y.-W. Zhong, and E. Nakamura Organometallics 25 2006 2826 2832
14. D. Carmona, M.P. Lamata, F. Viguri, R. Rodríguez, C. Barba, F.J. Lahoz, M.L. Martín, L.A. Oro, and L. Salvatella Organometallics 26 2007 6493 6496
15. D. Carmona, M.P. Lamata, F. Viguri, R. Rodríguez, L.A. Oro, A.I. Balana, F.J. Lahoz, T. Tejero, P. Merino, S. Franco, and I. Montesa J. Am. Chem. Soc. 126 2004 2716 2717
16. M. Sawamura, and Y. Ito Chem. Rev. 92 1992 857 871
17. A. Börner Eur. J. Inorg. Chem. 2001 327 337
18. A. Theil, J. Hitce, P. Retailleau, and A. Marinetti Eur. J. Org. Chem. 2006 154 161
19. M. Sawamura, Y. Nakayama, T. Kato, and Y. Ito J. Org. Chem. 60 1995 1727 1732
20. C.R. Landis, R.A. Sawyer, and E. Somsook Organometallics 19 2000 994 1002
21. H.-U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, and M. Studer Adv. Synth. Catal. 345 2003 103 151
22. U. Nagel Angew. Chem., Int. Ed. Engl. 23 1984 435 436
23. K. Achiwa J. Am. Chem. Soc. 98 1976 8265 8266
24. G.L. Baker, S.J. Fritschel, J.R. Stille, and J.K. Stille J. Org. Chem. 46 1981 2954 2960
25. Y.-Y. Yan, and T.V. RajanBabu J. Org. Chem. 65 2000 900 906
26. J. Holz, M. Quirmbach, and A. Börner Synthesis 1997 983 1006
27. A. Börner, J. Ward, W. Ruth, J. Holz, A. Kless, D. Heller, and H.B. Kagan Tetrahedron 50 1994 10419 10430
28. D.K. Wicht, and D.S. Glueck A. Togni, H. Grutzmacher, Catalytic Hetero-functionalization 2001 Wiley-VCH Weinheim, Germany 143 170
29. C. Baillie, and J. Xiao Curr. Org. Chem. 7 2003 477 514
30. I.L. Odinets, N.M. Vinogradova, E.V. Matveeva, and T.A. Mastryukova Curr. Org. Chem. 9 2005 1899 1934
31. O. Delacroix, and A.C. Gaumont Curr. Org. Chem. 9 2005 1851 1882
32. B. Wiese, G. Knühl, D. Flubacher, J.W. Prieß, B. Ulriksen, K. Brödner, and G. Helmchen Eur. J. Org. Chem. 2005 3246 3262
33. D.K. Wicht, I.V. Kourkine, B.M. Lew, J.M. Nthenge, and D.S. Glueck J. Am. Chem. Soc. 119 1997 5039 5040
34. A.D. Sadow, and A. Togni J. Am. Chem. Soc. 127 2005 17012 17024
35. W.C. Yeo, S.Y. Tee, H.B. Tan, G.K. Tan, L.L. Koh, and P.H. Leung Inorg. Chem. 43 2004 8102 8109
36. S.A. Pullarkat, Y. Ding, Y. Li, G.K. Tan, and P.H. Leung Inorg. Chem. 45 2006 7455 7463
37. Y. Zhang, S.A. Pullarkat, Y. Li, and P.H. Leung Inorg. Chem. 48 2009 5535 5539
38. Y. Zhang, L. Tang, S.A. Pullarkat, F. Liu, Y. Li, and P.H. Leung J. Organomet. Chem. 694 2009 3500 3505
39. M.L. Bungabong, K.W. Tan, Y. Li, S.V. Selvaratnam, K.G. Dongol, and P.H. Leung Inorg. Chem. 46 2007 4733 4736
40. Y. Zhang, L. Tang, Y. Ding, J.H. Chua, Y. Li, M. Yuan, and P.H. Leung Tetrahedron Lett. 49 2008 1762 1767
41. M. Yuan, S.A. Pullarkat, M. Ma, Y. Zhang, Y. Huang, Y. Li, A. Goel, and P.H. Leung Organometallics 28 2009 780 786
42. L. Tang, Y. Zhang, D. Luo, Y. Li, K.F. Mok, W.C. Yeo, and P.H. Leung Tetrahedron Lett. 48 2007 33 35
43. Y. Huang, S.A. Pullarkat, M. Yuan, Y. Ding, Y. Li, and P.H. Leung Organometallics 29 2010 536 542
44. S. Kawasaki, A. Nakamura, K. Toyota, and M. Yoshifuji Bull. Chem. Soc. Jpn. 78 2005 1110 1120
45. C.C. Marvin, E.A. Voight, J.M. Suh, C.L. Paradise, and S.D. Burke J. Org. Chem. 73 2008 8452 8457
46. H. Kromann, M. Larsen, T. Boesen, K. Schønning, and S.F. Nielsen Eur. J. Med. Chem. 39 2004 993 1000
47. D.P. Papahatjis, V.R. Nahmias, S.P. Nikas, T. Andreou, S.O. Alapafuja, A. Tsotinis, J. Guo, P. Fan, and A. Makriyannis J. Med. Chem. 50 2007 4048 4060
48. C.V. Magatti, J.J. Kaminski, and I. Rothberg J. Org. Chem. 56 1991 3102 3108
49. G.R. Newkome, S. Arai, F.R. Fronczek, C.N. Moorefield, X. Lin, and C.D. Weis J. Org. Chem. 58 1993 898 903
50. M. Ravindranathan, N. Kalyanam, and S. Sivaram J. Org. Chem. 47 1982 4812 4813
51. T. Frejd, and T. Klingstedt Synthesis 1987 40 42
52. R. Badorrey, C. Cativiela, M.D. Díaz-de-Villegas, J.A. Gálvez, and A. Gil Tetrahedron: Asymmetry 14 2003 2209 2214
53. M. Fitz, E. Forró, E. Vigóczki, L. Lázár, and F. Fülöp Tetrahedron: Asymmetry 19 2008 1114 1119
54. Without addition of NaI, the reaction will yield the dichloro palladium complex like products 10b and 10c. However, the solubility of the dichloro analog of complex 10a is too poor for characterization.
55. A. Miyashita, A. Yasuda, H. Takaya, K. Toriumi, T. Ito, T. Souchi, and R. Noyori J. Am. Chem. Soc. 102 1980 7932 7934
56. R. Schmid, M. Cereghetti, B. Heiser, P. Schnholzer, and H.J. Hansen Helv. Chim. Acta 71 1988 897 929
57. D.C.R. Hockless, P.A. Gugger, P.H. Leung, R.C. Mayadunne, M. Pabel, and S.B. Wild Tetrahedron 53 1997 4083 4094
58. D.G. Allen, G.M. McLaughlin, G.B. Robertson, W.L. Steffen, G. Salem, and S.B. Wild Inorg. Chem. 21 1982 1007 1014
59. S.Y.M. Chooi, S.Y. Siah, P.H. Leung, and K.F. Mok Inorg. Chem. 32 1993 4812 4818