Sterically hindered mono(phosphines) as supporting ligands for the platinum-catalyzed hydroamination of amino alkenes

Organometallics

Volumn 27, Issue 10, 2008, Pages 2356-2358

  Bender, Christopher F ^a   Hudson, William B ^a   Widenhoefer, Ross A ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(Z) ALKENES; ACTIVE CATALYSTS; HYDRO AMINATION; INTRAMOLECULAR HYDROAMINATION; PHOSPHINES (PH3);

AMINES; CATALYSIS; HYDROCARBONS; LIGANDS; OLEFINS; PHOSPHORUS COMPOUNDS; PLATINUM;

AMINATION;

EID: 44649159029     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om8000982     Document Type: Article

References (80)

1. Liddell, J. R. Nat. Prod. Rep. 2002, 19, 773.
2. Michael, J. P. Nat. Prod. Rep. 2001, 18, 520.
3. Mitchinson, A.; Nadin, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862.
4. King, A. G.; Meinwald, J. Chem. Rev. 1996, 96, 1105.
5. Daly, J. W.; Garraffo, H. M.; Spande, T. F. Alkaloids: Chem. Pharmacol. 1993, 43, 185-288.
6. Daly, J. W. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 9-13.
7. Collins, M. A. Alkaloids: Chem. Pharmacol. 1983, 21, 329-358.
8. Brossi, A. Alkaloids: Chem. Pharmacol. 1993, 43, 119-183.
9. Ashby, J.; Elliot, B. M. In Comprehensive Heterocyclic Chemistry; Katrinsky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 1, pp 111-141.
10. Landquist, J. K. In Comprehensive Heterocyclic Chemistry; Katrinsky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 1; pp 143-183..
11. Mitsunobu, O. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol 6, pp 65-101.
12. Bird, C. W.; Cheeseman, G. W. H. In Comprehensive Heterocyclic Chemistry; Katrinsky, A., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 4, pp 89-153.
13. McKillop, A.; Boulton, A. J. In Comprehensive Heterocyclic Chemistry; Katrinsky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 2, pp 67-98.
14. Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337.
15. Beller, M.; Tillack, A.; Seayad, J. In Transition Metals for Organic Synthesis, 2nd ed.; Wiley-VCH: Weinheim, 2004; pp 403-414.
16. Han, X.; Widenhoefer, R. A. Eur. J. Org. Chem. 2006, 4555.
17. Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368.
18. Brunet, J. J. Neibecker, D. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: Weinheim, 2001; pp 91-142.
19. Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104.
20. Hong, S.; Marks, T. J. Acc Chem. Res. 2004, 37, 673.
21. Riegert, D.; Collin, J.; Meddour, A.; Schulz, E.; Trifonov, A. J. Org. Chem. 2006, 71, 2514.
22. Kim, J. Y.; Livinghouse, T. Org. Lett. 2005, 7, 4391.
23. Kim, J. Y.; Livinghouse, T. Org. Lett. 2005, 7, 1737.
24. Gribkov, D. V.; Hultzsch, K. C.; Hampel, F. J. Am. Chem. Soc. 2006, 128, 3748.
25. Molander, G. A.; Dowdy, E. D. J. Org. Chem. 1999, 64, 6515.
26. Kim, Y. K.; Livinghouse, T.; Horino, Y. J. Am. Chem. Soc. 2003, 125, 9560.
27. Martinez, P. H.; Hultzsch, K. C.; Hampel, F. Chem. Commun. 2006, 2221.
28. Ogata, T.; Ujihara, A.; Tsuchida, S.; Shimizu, T.; Kaneshige, A.; Tomioka, K. Tetrahedron Lett. 2007, 48, 6648.
29. Quinet, C.; Jourdain, P.; Hermans, C.; Ates, A.; Lucas, I.; Markó, I. E. Tetrahedron 2008, 64, 1077.
30. Crimmin, M. R.; Casely, I. J.; Hill, M. S. J. Am. Chem. Soc. 2005, 127, 2042.
31. Müller, C.; Loos, C.; Schulenberg, N.; Doye, S. Eur. J. Org. Chem. 2006, 2499.
32. Kim, H.; Lee, P. H.; Livinghouse, T. Chem. Commun. 2005, 5205.
33. Thompson, R. K.; Bexrud, J. A.; Schafer, L. L. Organometallics 2006, 25, 4069.
34. Bexrud, J. A.; Beard, J. D.; Leiten, D. C.; Schafer, L. L Org. Lett. 2005, 7, 1959.
35. Wood, M. C.; Leitch, D. C.; Yeung, C. S.; Kozak, J. A.; Schafer, L. L. Angew. Chem., Int. Ed. 2007, 46, 354.
36. Gott, A. L.; Clarke, A. J.; Clarkson, G. J.; Scott, P. Organometallics 2007, 26, 1729.
37. Knight, P. D.; Munslow, L.; O'Shaughnessy, P. N.; Scott, P. Chem. Commun. 2004, 894.
38. Gribkov, D. V.; Hultzsch, K. C. Angew. Chem., Int. Ed. 2004, 43, 5542.
39. Watson, D. A.; Chiu, M.; Bergman, R. G. Organometallics 2006, 25,4731.
40. Kim, H.; Kim, Y. K.; Shim, J. H.; Kim, M.; Han, M.; Livinghouse, T.; Leea, P. H. Adv. Synth. Catal. 2006, 348, 2609.
41. Stubbert, B. D.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 6149.
42. Ackermann, L.; Kaspar, L. T.; Althammer, A. Org. Biomol. Chem. 2007, 5, 1975.
43. Takemiya, A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 6042.
44. Sakai, N.; Ridder, A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 8134.
45. Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2005, 127, 1070.
46. Palumbo, R.; De Renzi, A.; Panunzi, A.; Paiaro, G. J. Am. Chem. Soc. 1969, 91, 3874.
47. Panunzi, A.; De Renzi, A.; Palumbo, R.; Paiaro, G. J. Am. Chem. Soc. 1969, 91, 3879.
48. Kaplan, P. D.; Schmidt, P.; Orchin, M. J. Am. Chem. Soc. 1968, 90, 4175.
49. Pryadun, R.; Sukumaran, D.; Bogadi, R.; Atwood, J. D. J. Am. Chem. Soc. 2004, 126, 12414.
50. Liu, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 1570.
51. Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 5961.
52. Jenkins, H. A.; Yap, G. P. A.; Puddephatt, R. J. Organometallics 1997, 16, 1946.
53. Johansson, L.; Tilset, M. J. Am. Chem. Soc. 2001, 123, 739.
54. Prokopchuk, E. M.; Puddephatt, R. J. Organometallics 2003, 22, 787.
55. Hill, G. S.; Rendina, L. M.; Puddephatt, R. J. Organometallics 1995, 14, 4966.
56. Crumpton-Bregel, D. M.; Goldberg, K. I. J. Am. Chem. Soc. 2003, 125, 9442.
57. Fekl, U.; Zahl, A.; van Eldik, R. Organometallics 1999, 18, 4156.
58. De Felice, V.; De Renzi, A.; Panunzi, A.; Tesauro, D. J. Organomet. Chem. 1995, 488, C13.
59. Hinman, J. G.; Baar, C. R.; Jennings, M. C.; Puddephatt, R. J. Organometallics 2000, 19, 563.
60. Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224.
61. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382.
62. Culkin, D. A.; Hartwig, J. F. Organometallics 2004, 23, 3398.
63. Ziegler, C. B.; Heck, R. F. J. Org. Chem. 1978, 43, 2941.
64. Kim, J-I. I.; Patel, B. A.; Heck, R. F. J. Org. Chem. 1981, 46, 1067.
65. Spencer, A. J. Organomet. Chem. 1983, 258, 101.
66. Harris, G. D.; Herr, R. J.; Weinreb, S. M. J. Org. Chem. 1992, 57, 2528.
67. Hay, M. B.; Wolfe, J. P. J. Am. Chem. Soc. 2005, 127, 16468.
68. Hensel, V.; Lützow, K.; Jacob, J.; Gessler, K.; Saenger, W.; Schlüter, A.-D. Angew. Chem., Int. Ed. Engl. 1997, 36, 2654.
69. Chmil, K.; Scherf, U. Makromol. Chem. 1993, 194, 1377.
70. Rau, I. U.; Rehahn, M. Makromol. Chem. 1993, 194, 2225.
71. Tanigaki, N.; Masuda, H.; Kaeriyama, K. Polymer 1997, 38, 1221.
72. Koch, F.; Hietz, W. Makromol. Chem. Phys. 1997, 198, 1531.
73. Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441.
74. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
75. Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848.
76. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 2046.
77. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
78. Tolman, C. A. Chem. Rev. 1977, 77, 313.
79. Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360.
80. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.