The Pauson-Khand reaction: A gas-phase and solution-phase examination using electrospray ionization mass spectrometry

Organometallics

Volumn 30, Issue 20, 2011, Pages 5471-5479

  Henderson, Matthew A ^a   Luo, Jingwei ^a   Oliver, Allen ^b   McIndoe, J Scott ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

^b UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE LIGANDS; CO LIGANDS; DICOBALT HEXACARBONYL; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; ENTROPY OF ACTIVATION; GASPHASE; HEXACARBONYL COMPLEX; INTERMOLECULAR REACTIONS; INTRAMOLECULAR REACTIVITY; LIGAND DISSOCIATION; PAUSON-KHAND REACTIONS; PENTACARBONYL; RATE LIMITING;

ACETYLENE; ASSOCIATION REACTIONS; BIOACTIVITY; ELECTROSPRAY IONIZATION; IONIZATION OF GASES; LIGANDS; MASS SPECTROMETRY; OLEFINS;

REACTION INTERMEDIATES;

EID: 80054740662     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200717r     Document Type: Article

References (77)

1. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. Chem. Commun. 1971, 36
2. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J. Chem. Soc., Perkin Trans. 1 1973, 975-977
3. Pauson, P. L. Tetrahedron 1985, 41, 5855-5860
4. Magnus, P.; Principe, L. M.; Slater, M. J. J. Org. Chem. 1987, 52, 1483-1486
5. Blanco-Urgoiti, J.; Anorbe, L.; Perez-Serrano, L.; Dominguez, G.; Perez-Castells, J. Chem. Soc. Rev. 2004, 33, 32-42
6. Fletcher, A. J; Christie, S. D. R. J. Chem. Soc., Perkin Trans. 1 2000, 1657-1668
7. Gibson, S. E.; Mainolfi, N. Angew. Chem., Int. Ed. Engl. 2005, 44, 3022-3037
8. Green, J. R. Curr. Org. Chem. 2001, 5, 809-826
9. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc. Perkin Trans. 1 1973, 977-981
10. Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. Engl. 1998, 37 (7) 911-914
11. Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2801-2804
12. Sugihara, T.; Yamada., M.; Yamaguchi, M.; Nishizawa, M. Synlett 1999, 771-773
13. Billington, D. C.; Helps, I. M.; Pauson, P. L.; Thomson, W.; Willison, D. J. Organomet. Chem. 1988, 354, 233-242
14. Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384-1386
15. Hanson, B. E. Comments Inorg. Chem. 2002, 23, 289-318
16. Wang, H.; Sawyer, J. R.; Evans, P. A.; Baik, M-.J. Angew. Chem., Int. Ed. Engl. 2008, 47, 342-345
17. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285-2286
18. Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762-3765
19. Kobayashi, T.; Koga, Y.; Narasaka, K. J. Organomet. Chem. 2001, 624, 73-87
20. Jeong, N.; Ki Sung, B.; Sung Kim, J.; Bong Park, S.; Deok Seo, S.; Young Shin, J.; Yeol In, K.; KyungChoi, Y. Pure Appl. Chem. 2002, 74, 85-91
21. Mukai, C.; Uchiyama, M.; Hanaoka, M. J. Chem. Soc., Chem. Commun. 1992, 1014-1015
22. Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115 (3) 1154-1156
23. Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336-3346
24. Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202-203
25. Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656-1661
26. Mastrorilli, P.; Nobile, C. F.; Paolillo, R.; Suranna, G. P. J. Mol. Catal. A: Chem. 2004, 214, 103-106
27. Magnus, P.; Exon, C.; Albaugh-Robertson, P. Tetrahedron 1985, 41 (24) 5861-5869
28. Rautenstrauch, V.; Megard, P.; Conesa, J.; Kuster, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 1413-1416
29. Yamanaka, M.; Nakamura, E. J. Am. Chem. Soc. 2001, 123, 1703-1708
30. Gordon, C. M.; Kiszka, M.; Dunkin, I. R.; Kerr, W. J.; Scott, J. S.; Gebicki, J. J. Organomet. Chem. 1998, 554, 147-154
31. Banide, E. V.; Muller-Bunz, H.; Manning, A. R.; Evans, P.; McGlinchey, M. J. Angew. Chem., Int. Ed. 2007, 46, 2907-2910
32. Pallerla, M. K.; Yap, G. P. A.; Fox, J. M. J. Org. Chem. 2008, 73, 6137-6141
33. de Bruin, T. J. M.; Milet, A.; Greene, A. E.; Gimbert, Y. J. Org. Chem. 2004, 69, 1075-1080
34. Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207
35. Verdaguer, X.; Vazquez, J.; Fuster, G.; Bernardes-Genisson, V.; Greene, A. E.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1998, 63, 7037-7052
36. Cabot, R.; Lledo, A.; Reves, M.; Riera, A.; Verdaguer, X. Organometallics 2007, 26, 1134-1142
37. Blackmond, D. G. Angew. Chem., Int. Ed. 2005, 44, 4302-4320
38. Jackson, S. M.; Chisholm, D. M.; McIndoe, J. S.; Rosenberg, L. Eur. J. Inorg. Chem. 2011, 327-330
39. Santos, L. S., Ed. Reactive Intermediates: MS Investigations in Solution; Wiley-VCH: Weinheim, Germany, 2010.
40. Rylander, P. N., Organic Syntheses with Noble Metal Catalysts; Academic Press: New York, 1973.
41. Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D., Application of Transition Metal Catalysts in Organic Synthesis; Springer: New York, 1999.
42. Jones, W. H., Ed. Catalysis in Organic Synthesis; Academic Press: Toronto, 1980.
43. Heaton, B., Ed. Mechanisms in Homogeneous Catalysis; Wiley-VCH: Weinheim, Germany, 2005.
44. Henderson, W.; Evans, C. Inorg. Chim. Acta 1999, 294, 183-192
45. Santos, L. S.; Rosso, G. B.; Pilli, R. A.; Eberlin, M. N. J. Org. Chem. 2007, 72, 5809-5812
46. Decker, C.; Henderson, W.; Nicholson, B. K. J. Chem. Soc., Dalton Trans. 1999, 3507-3513
47. Farrer, N. J.; McDonald, R.; McIndoe, J. S. Dalton Trans. 2006, 4570-4579
48. Farrer, N. J.; McDonald, R.; Piga, T.; McIndoe, J. S. Polyhedron 2010, 29, 254-261
49. Henderson, W.; Nicholson, B. K. J. Chem. Soc., Chem. Commun. 1995, 2531-2532
50. Henderson, W.; McIndoe, J. S.; Nicholson, B. K.; Dyson, P. J. J. Chem. Soc., Dalton Trans. 1998, 519-525
51. Hinderling, C.; Adlhart, C.; Chen, P. Angew. Chem., Int. Ed. 1998, 37, 2685-2689
52. Chisholm, D. M.; Oliver, A. G.; McIndoe, J. S. Dalton Trans. 2010, 39, 364-373
53. Adlhart, C.; Chen, P. Helv. Chim. Acta 2000, 83, 2192-2196
54. Crawford, E.; Lohr, T.; Leitao, E. M.; Kwok, S.; McIndoe, J. S. Dalton Trans. 2009, 9110-9112
55. Gimbert, Y.; Lesage, D.; Milet, A.; Fournier, F.; Greene, A. E.; Tabet, J. C. Org. Lett. 2003, 5, 4073-4075
56. Fei, Z.; Zhao, D.; Scopelliti, R.; Dyson, P. J. Organometallics 2004, 23, 1622-1628
57. Butcher, C. P. G.; Dyson, P. J.; Johnson, B. F. G.; Khimyak, T.; McIndoe, J. S. Chem. Eur. J. 2003, 9, 944-950
58. Crawford, E.; Dyson, P. J.; Forest, O.; Kwok, S.; McIndoe, J. S. J. Cluster Sci. 2006, 17, 47-63
59. Henderson, M. A.; Kwok, S.; McIndoe, J. S. J. Am. Soc. Mass Spectrom. 2009, 20, 658-666
60. Billington, D. C.; Helps, M. I.; Pauson, P. L.; Thomson, W.; Willison, D. J. Organomet. Chem. 1998, 354, 233-242
61. Vikse, K. L.; Woods, M. P.; McIndoe, J. S. Organometallics 2010, 29, 6615-6618
62. Vikse, K. L.; Ahmadi, Z.; Manning, C. C.; Harrington, D. A.; McIndoe, J. S. Angew. Chem., Int. Ed. 2011, 50, 8304-8306
63. Allian, A. D.; Tjahjono, M.; Garland, M. Organometallics 2006, 25, 2182-2188
64. Pearson, A. J.; Shively, R. J., Jr.; Dubbert, R. A. Organometallics 1992, 11, 4096-4104
65. Maryanoff, B. E.; Zhang, H. C. Arkivoc 2007, 7, 7-35
66. Rausch, B. J.; Gleiter, R.; Rominger, F. Dalton Trans. 2002, 2219-2226
67. Roy, S. K.; Basak, A. Chem. Commun. 2006, 1646-1648
68. Pearson, A. J.; Shively, R. J., Jr. Organometallics 1994, 13, 578-584
69. Battaglia, L.P.; Delledonne, D.; Nardelli, M.; Predieri, G.; Chiusoli, G. P.; Costa, M.; Pelizzi, C. J. Organomet. Chem. 1989, 363, 209-222
70. Krafft, M. E.; Boñaga, L. V. R.; Hirosawa, C. J. Org. Chem. 2001, 66, 3004-3020
71. APEX-II v 2008-1, Bruker AXS, Madison, WI.
72. Sheldrick, G. M. SADABS; University of Göttingen, Göttingen, Germany, 2008.
73. Sheldrick, G. M. XPREP; University of Göttingen, Göttingen, Germany, 2008.
74. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112
75. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565
76. http://www.povray.org/
77. De Vynck, V.; Goethals, E. J. Macromol. Rapid Commun. 1997, 18, 149-156