New insights into the mechanism of palladium-catalyzed allylic amination

Journal of the American Chemical Society

Volumn 127, Issue 49, 2005, Pages 17516-17529

  Watson, Iain D G ^a   Yudin, Andrei K ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINES; CATALYST ACTIVITY; ISOMERIZATION; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ALIPHATIC ALLYL ACETATES; AZIRIDINES;

PALLADIUM COMPOUNDS;

ALLYL COMPOUND; AZIRIDINE DERIVATIVE; NITROGEN DERIVATIVE; PALLADIUM COMPLEX;

AMINATION; ARTICLE; BINDING KINETICS; CATALYSIS; COMPLEX FORMATION; CROSSING OVER; ISOMERIZATION; LIGAND BINDING; METAL BINDING; MOLECULAR STABILITY; PROTEIN QUATERNARY STRUCTURE; REGULATORY MECHANISM; STEREOCHEMISTRY; SUBSTITUTION REACTION; THERMODYNAMICS;

EID: 29044433582     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055288c     Document Type: Article

References (104)

1. Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, Germany, 2006.
2. Watson, I. D. G.; Yudin, A. K. Curr. Opin. Drug Discovery Dev. 2002, 5, 906-917.
3. (a) Alezra, V.; Bouchet, C.; Micouin, L.; Bonin, M.; Husson, H.-P. Tetrahedron Lett. 2000, 41, 655-658.
4. (b) Alezra, V.; Bonin, M.; Micouin, L.; Policar, C.; Husson, H.-P. Eur. J. Org. Chem. 2001, 2589-2594.
5. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
6. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14.
7. (a) Burgess, K.; Liu, L. T.; Pal, B. J. Org. Chem. 1993, 58, 4758-4763.
8. (b) Bower, J. F.; Jumnah, R.; Williams, A. C.; Williams, J. M. J. J. Chem. Soc., Perkin Trans. 1 1997, 1411-1420.
9. (c) Ichikawa, Y.; Ito, T.; Nishiyama, T.; Isobe, M. Synlett 2003, 1034-1036.
10. (d) Ito, K.; Akashi, S.; Saito, B.; Katsuki, T. Synlett 2003, 1809-1812.
11. (e) Paquette, L. A.; Leit, S. M. J. Am. Chem. Soc. 1999, 121, 8126-8127.
12. (f) Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron 1995, 51, 11087-11110.
13. (g) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005.
14. (h) Liu, H.; Liang, X.; Sohoel, H.; Buelow, A.; Bols, M. J. Am. Chem. Soc. 2001, 123, 5116-5117.
15. Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444-458.
16. Ricci, A. Modern Amination Methods; Wiley-VCH: Weinheim, Germany, 2000.
17. (a) Mitsunobu, O. Synthesis 1981, 1-28.
18. (b) Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127-164.
19. (c) Wisniewski, K.; Koldziejczyk, A. S.; Falkiewicz, B. J. Pept. Sci. 1998, 4, 1-14.
20. (d) Nune, S. K. Synlett 2003, 1221-1222.
21. Trost, B. M.; VanVranken, D. L. Chem. Rev. 1996, 96, 395-422.
22. (a) Watson, I. D. G.; Styler, S. A.; Yudin, A. K. J. Am. Chem. Soc. 2004, 126, 5086-5087.
23. (b) Sasaki, M.; Yudin, A. K. J. Am. Chem. Soc. 2003, 125, 14242-14243.
24. (c) Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530-531.
25. (d) Watson, I. D. G.; Yudin, A. K. J. Org. Chem. 2003, 68, 5160-5167.
26. (a) Atkins, K. E.; Walker, W. E.; Manyik, R. M. Tetrahedron Lett. 1970, 11, 3821-3824.
27. (b) Kinoshita, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 4085-4088.
28. We have observed a lack of reactivity of carbonyl-containing aziridines in other transition metal-catalyzed processes: Chen, G.; Yudin, A. K. 2004, The University of Toronto, Toronto, Canada, unpublished results.
29. (a) Lee, W. K.; Ha, H.-J. Aldrichimica Acta 2003, 36, 57-63.
30. (b) Cardillo, G.; Gentilucci, L.; Tolomelli, A. Aldrichimica Acta 2003, 36, 39-50.
31. Kodama, H.; Taiji, T.; Ohta, T.; Furukawa, I. Synlett 2001, 385-387.
32. Dierkes, P.; van Leeuwen, P. J. Chem. Soc., Dalton Trans. 1999, 1519-1529.
33. Riddick, J. A.; Hunger, W. B. Organic Solvents: Physical Properties and Methods of Purification, 3rd ed.; Techniques of Organic Chemistry; Wiley-Interscience: New York, 1970; Vol. II.
34. We believe that the lower regioselectivity in this case results from some isomerization of the ring-opened product as the ring-opening step is performed in the presence of Pd catalyst (one-pot procedure).
35. 4 in THF at 60 °C gives full conversion to the background products in 6 h. See also the following references: (a) Keinan, E.; Kumar, S.; Dangur, V.; Vaya, J. J. Am. Chem. Soc. 1994, 116, 11151-11152.
36. (b) Andersson, P. G.; Schab, S. Organometallics 1995, 14, 1-2.
37. (a) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730-4743.
38. (b) Granberg, K. L.; Backvall, J. E. J. Am. Chem. Soc. 1992, 114, 6858-6863.
39. (c) Granberg, K. L.; Backvall, J. E. J. Am. Chem. Soc. 1994, 116, 10853-10853.
40. (a) Trost, B. M.; Keinan, E. J. Org. Chem. 1979, 44, 3451-3457.
41. (b) Åkermark, B.; Vitagliano, A. Organometallics 1985, 4, 1275-1283.
42. (c) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165-2166.
43. (d) Murahashi, S.-I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292-3303.
44. (e) Hutchins, R. O.; Wei, J.; Rao, S. J. J. Org. Chem. 1994, 56, 4007-4009.
45. (a) Kiener, C. A.; Shu, C.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14272-14273.
46. (b) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165.
47. (c) Shu, C. T.; Leitner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797-4800.
48. (d) Takeuchi, R.; Ue, N.; Tanabe, K.; Yamashita, K.; Shiga, N. J. Am. Chem. Soc. 2001, 123, 9525-9534.
49. (e) Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269-3271.
50. (f) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761-6762.
51. (g) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 12214-12214.
52. (h) Belda, O.; Moberg, C. Acc. Chem. Res. 2004, 37, 159-167.
53. (i) Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1982, 104, 5543-5545.
54. (j) Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1987, 109, 1469-1478.
55. (k) Trost, B. M.; Fraisse, P. L.; Ball, Z. T. Angew. Chem., Int. Ed. 2002, 41, 1059-1061.
56. (a) You, S.-L.; Zhu, X.-Z.; Luo, Y.-M.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2001, 123, 7471-7472.
57. (b) Hayashi, T.; Kishi, K.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1990, 31, 1743-1746.
58. (c) Faller, J. W.; Wilt, J. C. Org. Lett. 2004, 45, 7613-7616.
59. (d) Faller, J. W.; Wilt, J. C. Org. Lett. 2005, 7, 633-636.
60. (a) Hayashi, T.; Konishi, M.; Yokota, K. I.; Kumada, M. J. Organomet. Chem. 1985, 285, 359-373.
61. (b) Matsushita, H.; Negishi, E. J. Chem. Soc., Chem. Commun. 1982, 160-161.
62. (c) Kurosawa, H.; Kajimaru, H.; Ogoshi, S.; Yoneda, H.; Miki, K.; Kasai, N.; Murai, S.; Ikeda, I. J. Am. Chem. Soc. 1992, 114, 8417-8424.
63. (d) Sheffy, F. K.; Godschalx, J. P.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4833-4840.
64. (e) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019-3023.
65. (f) Trost, B. M.; Yoshida, J.; Lautens, M. J. Am. Chem. Soc. 1983, 105, 4494-4496.
66. (g) Matsumoto, Y.; Ohno, A.; Hayashi, T. Organometallics 1993, 12, 4051-4055.
67. (h) Trost, B. M.; Spagnol, M. D. J. Chem. Soc., Perkin Trans. 1 1995, 2083-2096.
68. (i) Kobayashi, Y.; Mizojiri, R.; Ikeda, E. J. Org. Chem. 1996, 61, 5391-5399.
69. (j) Murahashi, S. I.; Imada, Y.; Taniguchi, Y.; Higashiura, S. J. Org. Chem. 1993, 58, 1538-1545.
70. (k) Keinan, E.; Greenspoon, N. Tetrahedron Lett. 1982, 23, 241-244.
71. Moreno-Manas, M.; Morral, L.; Pleixats, R. J. Org. Chem. 1998, 63, 6160-6166.
72. (a) Evans, P. A.; Nelson, J. D. Tetrahedron Lett. 1998, 39, 1725-1728.
73. (b) Evans, P. A.; Leahy, D. K. J. Am. Chem. Soc. 2000, 122, 5012-5013.
74. Evans, P. A.; Kennedy, L. J. Org. Lett. 2000, 2, 2213-2215.
75. Evans, P. A.; Kennedy, L. J. J. Am. Chem. Soc. 2001, 123, 1234-1235.
76. (a) Lloyd-Jones, O. C.; Stephen, S. C.; Murray, M.; Butts, C. P.; Vyskocil, S.; Kocovsky, P. Chem. Eur. J. 2000, 6, 4348-4357.
77. (b) Lloyd-Jones, G. C.; Stephen, S. C. Chem. Eur. J. 1998, 4, 2539-2549.
78. (c) Lloyd-Jones, G. C.; Stephen, S. C. Chem. Commun. 1998, 2321-2322.
79. (d) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738-7748.
80. (e) Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681-1687.
81. Some σ-allyl palladium complexes have been structurally characterized: (a) Kollmar, M.; Helmchen, G. Organometallics 2002, 21, 4771-4775.
82. (b) Braunstein, P.; Naud, F.; Dedieu, A.; Rohmer, M.-M.; DeCian, A.; Rettig, S. Organometallics 2001, 20, 2966-2981.
83. (a) Åkermark, B.; Åkermark, G.; Hegedus, L. S.; Zetterberg, K. J. Am. Chem. Soc. 1981, 103, 3037-3040.
84. (b) Amatore, C.; Jutand, A.; Meyer, G.; Mottier, L. Chem. Eur. J. 1999, 5, 466-473.
85. (c) Bouquillon, S.; Muzart, J. Eur. J. Org. Chem. 2001, 3301-3305.
86. Thibault, C.; Génin, E.; Giroud, C.; Meyer, G.; Jutand, A. J. Organomet. Chem. 2003, 687, 365-376 and references therein.
87. (a) Powell, J.; Shaw, B. L. J. Chem. Soc. A 1967, 1839-1851.
88. (b) Kurosawa, H. J. Chem. Soc., Dalton Trans. 1979, 939.
89. Overman, L. E.; Knoll, F. M. Tetrahedron Lett. 1979, 20, 321-324.
90. 0. See the following references: (a) Amatore, C.; Carre, E.; Jutand, A.; Mbarki, M. A. Organometallics 1995, 14, 1818-1826.
91. (b) Amatore, C.; Jutand, A.; Thuilliez, A. Organometallics 2001, 20, 3241-3249.
92. (a) Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046-6047.
93. (b) Saeki, T.; Son, E. C.; Tamao, K. Org. Lett. 2004, 6, 617-619.
94. (a) Doi, T.; Yanagisawa, A.; Miyazawa, M.; Yamamoto, K. Tetrahedron: Asymmetry 1995, 6, 389-392.
95. (b) Hirao, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. J. Organomet. Chem. 1982, 236, 409-414.
96. For instance, monosubstituted olefins are known to be considerably more reactive than disubstituted olefins in Wacker oxidation: Nelson, D. J.; Li, R.; Brammer, C. J. Am. Chem. Soc. 2001, 123, 1564-1568.
97. Searles, S.; Tamres, M.; Block, F.; Quarterman, L. A. J. Am. Chem. Soc. 1956, 78, 4917-4920.
98. (a) Complexes between palladium and C-vinyl aziridines have been structurally characterized: BenCheikh, R.; Chaabouni, R.; Bonnet, M. C.; Dahan, F. Polyhedron 1998, 17, 185-192.
99. (b) Ferioli, F.; Fiorelli, C.; Martelli, G.; Monari, M.; Savoia, D.; Tobaldin, P. Eur. J. Org. Chem. 2005, 1416-1426.
100. (c) Tanner, D.; Andersson, P. G.; Harden, A.; Somfai, P. Tetrahedron Lett. 1994, 35, 4631-4634.
101. (d) Tanner, D.; Johansson, F.; Harden, A.; Andersson, P. G. Tetrahedron 1998, 54, 15731-15738.
102. The reverse is not the case: there is crossover when NH aziridine 1a is added to allylated branched 1,2,3,4-tetrahydroisoquinoline (13).
103. For recent use of Ir-catalyzed kinetic resolution of allyl acetates, see: Fischer, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1628-1629.
104. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.