Intramolecular hydroamination/cyclisation of aminoallenes mediated by a cationic zirconocene catalyst: A computational mechanistic study

Dalton Transactions

Volumn , Issue 35, 2006, Pages 4277-4285

  Tobisch, Sven ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINES; CHEMICAL BONDS; POSITIVE IONS;

METATHESIS-TYPE TRANSITION STATES;

CATALYSTS;

ALKADIENE; ALLENE; ORGANOMETALLIC COMPOUND; ZIRCONIUM; ZIRCONOCENE DICHLORIDE;

AMINATION; ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; THEORETICAL MODEL;

ALKADIENES; AMINATION; CATALYSIS; CYCLIZATION; MODELS, THEORETICAL; ORGANOMETALLIC COMPOUNDS; ZIRCONIUM;

EID: 33747861593     PISSN: 14779226     EISSN: 14779234     Source Type: Journal    
DOI: 10.1039/b605992a     Document Type: Article

References (105)

1. L. S. Hegedus Angew. Chem. 1988 100 1147
2. L. S. Hegedus Angew. Chem., Int. Ed. 1998 27 1113
3. D. M. Roundhill Catal. Today 1997 37 155
4. T. E. Müller M. Beller Chem. Rev. 1988 98 675
5. M. Nobis B. Drießen-Hölscher Angew. Chem. 2001 113 4105
6. M. Nobis B. Drießen-Hölscher Angew. Chem., Int. Ed. 2001 40 3983
7. R. Taube, in Applied Homogeneous Catalysis with Organometallic Complexes, ed., B. Cornils, and, W. A. Herrmann, Wiley-VCH, Weinheim, Germany, 2002, pp. 513-524
8. J. Seayad A. Tillack C. G. Hartung M. Beller Adv. Synth. Catal. 2002 344 795
9. F. Pohlki S. Doye Chem. Soc. Rev. 2003 32 104
10. P. W. Roesky T. E. Müller Angew. Chem. 2003 115 2812
11. P. W. Roesky T. E. Müller Angew. Chem., Int. Ed. 2003 42 2708
12. J. F. Hartwig Pure Appl. Chem. 2004 76 507
13. K. C. Hultzsch Adv. Synth. Catal. 2005 347 367
14. Y. K. Kim T. Livinghouse Angew. Chem. 2002 114 3797
15. Y. K. Kim T. Livinghouse Angew. Chem., Int. Ed. 2002 41 3645
16. Y. K. Kim T. Livinghouse Y. Horino J. Am. Chem. Soc. 2003 125 9560
17. P. N. O'Shaughnessy P. D. Knight C. Morton K. M. Gillespie P. Scott Chem. Commun. 2003 14 1770
18. D. V. Gribkov K. C. Hultzsch F. Hampel Chem. Eur. J. 2003 9 4796
19. S. Hong A. M. Kawaoka T. J. Marks J. Am. Chem. Soc. 2003 125 15878
20. J. Collin J.-C. Duran E. Schulz A. Trifonov Chem. Commun. 2003 3048
21. F. Lauterwasser P. G. Hayes St. Bräse W. E. Piers L. L. Schafer Organometallics 2004 23 2234
22. D. V. Gribkov K. C. Hultzsch Chem. Commun. 2004 730
23. K. C. Hultzsch F. Hampel Th. Wagner Organometallics 2004 23 2601
24. J. Y. Kim T. Livinghouse Org. Lett. 2005 7 4391
25. M. R. Gagné T. J. Marks J. Am. Chem. Soc. 1989 111 4108
26. M. R. Gagné T. J. Marks J. Am. Chem. Soc. 1992 114 275
27. Y. Li P.-F. Fu T. J. Marks Organometallics 1994 13 439
28. Y. Li T. J. Marks J. Am. Chem. Soc. 1996 118 9295
29. G. A. Molander E. D. Dowdy J. Org. Chem. 1998 63 8983
30. M. R. Bürgstein H. Berberich P. W. Roesky Organometallics 1998 17 1452
31. A. T. Gilbert B. L. Davis T. J. Emge R. D. Broene Organometallics 1999 18 2125
32. G. A. Molander E. D. Dowdy J. Org. Chem. 1999 64 6515
33. Y. K. Kim T. Livinghouse J. E. Bercaw Tetrahedron Lett. 2001 42 2944
34. G. A. Molander E. D. Dowdy S. K. Pack J. Org. Chem. 2001 66 4344
35. M. R. Bürgstein H. Berberich P. W. Roesky Chem. Eur. J. 2001 7 7078
36. S. Hong T. J. Marks J. Am. Chem. Soc. 2002 124 7886
37. S. Hong S. Tian M. V. Metz T. J. Marks J. Am. Chem. Soc. 2003 125 14768
38. A. Zulys T. K. Panda M. T. Gamer P. W. Roesky Chem. Commun. 2004 2584
39. G. A. Molander J. A. C. Romero Chem. Rev. 2002 102 2161
40. S. Hong T. J. Marks Acc. Chem. Res. 2004 37 673
41. P. L. McGrane T. Livinghouse J. Org. Chem. 1992 57 1323
42. P. L. McGrane M. Jensen T. Livinghouse J. Am. Chem. Soc. 1992 114 5459
43. P. L. McGrane T. Livinghouse J. Am. Chem. Soc. 1993 115 11485
44. I. Bytschkov S. Doye Tetrahedron Lett. 2002 43 3715
45. C. Li R. K. Thomson B. Gillon B. O. Patrick L. L. Schafer Chem. Commun. 2003 2462
46. D. V. Gribkov K. C. Hultzsch Angew. Chem. 2004 116 5659
47. D. V. Gribkov K. C. Hultzsch Angew. Chem., Int. Ed. 2004 43 5542
48. J. A. Bexrud J. D. Beard D. C. Leitch L. L. Schafer Org. Lett. 2005 7 1959
49. H. Kim P. H. Lee T. Livinghouse Chem. Commun. 2005 5205
50. T. Müller M. Grosche E. Herdtweck A.-K. Pleier E. Walter Y.-K. Yan Organometallics 2000 19 170
51. T. Kondo T. Okada T. Suzuki T. Mitsudo J. Organomet. Chem. 2001 622 149
52. S. Burling L. D. Field B. A. Messerle P. Turner Organometallics 2004 23 1714
53. L. M. Lutete I. Kadota Y. Yamamoto J. Am. Chem. Soc. 2004 126 1622
54. L. D. Field B. A. Messerle K. Q. Vuong P. Turner Organometallics 2005 24 4241
55. G. B. Bajracharya Z. Huo Y. Yamamoto J. Org. Chem. 2005 70 4883
56. M. R. Crimmin I. J. Caseley M. S. Hill J. Am. Chem. Soc. 2005 127 2042
57. A. Zylus M. Dochnahl D. Hollmann K. Löhnwitz J.-St. Hermann P. W. Roesky S. Blechert, S. Angew. Chem. 2005 117 7972
58. A. Zylus M. Dochnahl D. Hollmann K. Löhnwitz J.-St. Hermann P. W. Roesky S. Blechert, S. Angew. Chem., Int. Ed. 2005 44 7794
59. V. M. Arredondo F. E. McDonald T. J. Marks J. Am. Chem. Soc. 1998 120 4871
60. V. M. Arredondo S. Tian F. E. McDonald T. J. Marks J. Am. Chem. Soc. 1999 121 3633
61. V. M. Arredondo F. E. McDonald T. J. Marks Organometallics 1999 18 1949
62. S. Arseniyadis J. Gore Tetrahedron Lett. 1983 24 3997
63. R. Kinsman D. Lathbury P. Vernon T. Gallagher J. Chem. Soc., Chem. Commun. 1987 243
64. D. N. A. Fox T. Gallagher Tetrahedron 1990 46 4697
65. M. Al-Masum M. Meguro Y. Yamamoto Tetrahedron Lett. 1997 38 6071
66. M. Meguro Y. Yamamoto Tetrahedron Lett. 1998 39 5421
67. L. Ackermann R. G. Bergman Org. Lett. 2002 4 1475
68. L. Ackermann R. G. Bergman R. N. Loy J. Am. Chem. Soc. 2003 125 11956
69. J. M. Hoover J. R. Petersen J. H. Pikul A. R. Johnson Organometallics 2004 23 4614
70. J. R. Petersen J. M. Hoover W. S. Kassel A. L. Rheingold A. R. Johnson Inorg. Chim. Acta 2005 358 687
71. A. H. Hoyeda J. P. Morken Angew. Chem. 1996 108 1378
72. A. H. Hoyeda J. P. Morken Angew. Chem., Int. Ed. Engl. 1996 35 1262
73. P. A. Knight I. Munslow P. N. O'Shaughnessy P. Scott Chem. Commun. 2004 894
74. M. R. Gagné C. L. Stern T. J. Marks J. Am. Chem. Soc. 1992 114 275
75. V. M. Arredondo F. E. McDonald T. J. Marks J. Am. Chem. Soc. 1998 120 4871
76. A. Motta G. Lanza I. L. Fragala T. J. Marks Organometallics 2004 23 4097
77. S. Tobisch J. Am. Chem. Soc. 2005 127 11979
78. A. Motta I. L. Fragala T. J. Marks Organometallics 2005 24 4995
79. S. Tobisch Chem. Eur. J. 2006 12 2520
80. S. Tobisch Chem. Eur. J. 2005 11 6372
81. H. M. Senn P. E. Blöchl A. Togni J. Am. Chem. Soc. 2000 122 4098
82. B. F. Straub R. G. Bergman Angew. Chem. 2001 113 4768
83. B. F. Straub R. G. Bergman Angew. Chem., Int. Ed. 2001 40 4632
84. P. J. Walsh A. M. Baranger R. G. Bergman J. Am. Chem. Soc. 1992 114 1708
85. A. M. Baranger P. J. Walsh R. G. Bergman J. Am. Chem. Soc. 1993 115 2753
86. S. Y. Lee R. G. Bergman Tetrahedron 1995 51 4255
87. J. S. Johnson R. G. Bergman J. Am. Chem. Soc. 2001 123 2923
88. F. Pohlki S. Doye Angew. Chem. 2001 113 2361
89. F. Pohlki S. Doye Angew. Chem., Int. Ed. 2001 40 2305
90. R. Ahlrichs M. Bär M. Häser H. Horn C. Kölmel Chem. Phys. Lett. 1989 162 165
91. O. Treutler R. Ahlrichs J. Chem. Phys. 1995 102 346
92. K. Eichkorn O. Treutler H. Öhm M. Häser R. Ahlrichs Chem. Phys. Lett. 1995 242 652
93. P. A. M. Dirac Proc. Cambridge Philos. Soc. 1930 26 376
94. J. C. Slater Phys. Rev. 1951 81 385
95. S. H. Vosko L. Wilk M. Nussair Can. J. Phys. 1980 58 1200
96. A. D. Becke Phys. Rev. A: At., Mol., Opt. Phys. 1988 38 3098
97. J. P. Perdew Phys. Rev. B: Condens. Matter 1986 33 8822
98. J. P. Perdew Phys. Rev. B: Condens. Matter 1986 34 7406
99. A. Klamt G. Schüürmann J. Chem. Soc., Perkin Trans. 2 1993 799
100. A. Klamt, in Encyclopedia of Computational Chemistry, ed., P. von R. Schleyer, Wiley, Chichester, 1998, vol. 1, pp. 604-615
101. The reader is referred to Baldwin's rules for ring closure, which predict exo- and endocyclic paths to be favourable for aminoallenes. See, for instance: J. March, Advanced Organic Chemistry, Wiley, New York, 1992, 4th edn, pp. 212-214
102. This needs further elaboration for aminoallene substrates and/or precatalysts that are sterically more encumbered than reactants { 1 + 2} investigated herein. This crucial aspect, however, is beyond the scope of the present study and will be the subject of forthcoming investigations.
103. 7 centre of 5 is predicted to be kinetically impeded, thus being improbable, when compared to the path that commences from 5′ (Tables 3, S1, ESI).
104. The 1,3-hydrogen shift is presumably a viable process. The kinetics of this process has not been investigated in the present study
105. -1 (298.15 K).