Energetics and mechanism of organolanthanide-mediated phosphinoalkene hydrophosphination/cyclization. A density functional theory analysis

Organometallics

Volumn 24, Issue 21, 2005, Pages 4995-5003

  Motta, Alessandro ^c   Fragalà, Ignazio L ^a   Marks, Tobin J ^b  

^a UNIVERSITY OF CATANIA   (Italy)

^b NORTHWESTERN UNIVERSITY   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; MOLECULAR DYNAMICS; OLEFINS; PHOSPHORUS COMPOUNDS; PROTONS; SUBSTRATES;

ENERGETICS; HYDROPHOSPHINATION; PHOSPHINOALKENES; PROTONOLYSIS;

COMPLEXATION;

EID: 84962377248     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050570d     Document Type: Article

References (102)

1. For recent organolanthanide reviews, see: (a) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673-686.
2. (b) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850.
3. (c) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H, Chem. Rev. 2002, 102, 1851-1896.
4. (d) Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976.
5. (e) Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161-2186.
6. (f) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210.
7. (g) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226.
8. (h) Molander, G. A. Chemtracts: Org. Chem. 1998, 18, 237-263.
9. (i) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247-276.
10. (j) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2.
11. (k) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865-986.
12. (l) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362.
13. (m) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131-177.
14. (n) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
15. Hydrogenation: (a) Obora, Y.; Ohta, T.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1997, 119, 3745-3755.
16. (b) Roesky, P. W.; Denninger, U.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4486-4492.
17. (c) Haar, C. M.; Sern, C. L.; Marks, T. J. Organometallics 1996, 15, 1765-1784.
18. (d) Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091-8103.
19. Hydrosilylation: (a) Horino, Y.; Livinghouse, T. Organometallics 2004, 23, 12-14.
20. (b) Molander, G. A.; Corrette, C. P. Organometallics 1998, 17, 5504-5512.
21. (c) Schumann, H.; Keitsch, M. R.; Winterfeld, J.; Muhle, S.; Molander, G. A. J. Organomet. Chem. 1998, 559, 181-190.
22. (d) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157-7168.
23. (e) Molander, G. A.; Julius, M. J. Org. Chem. 1992, 57, 6347-6351.
24. (f) Sakakura, T.; Lautenschlager, H.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1991, 40-41.
25. Hydroboration: (a) Molander, G. A.; Pfeiffer, D. Org. Lett. 2001, 3, 361-363.
26. (b) Bijpost, E. A.; Duchateau, R.; Teuben, J. H. J. Mol. Catal. 1995, 95, 121-128.
27. (c) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220-9221.
28. (a) Koo, K.; Fu, P.-F.; Marks, T. J. Macromolecules 1999, 32, 981-988.
29. (b) Jia, L.; Yang, X.; Seyam, A. M.; Albert, I. D. L.; Fu, P.-F.; Yang, S.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 7900-7913.
30. (c) Jeske, G.; Schock, L. E.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8103-8110.
31. (d) Watson, P. L. J. Am. Chem. Soc. 1982, 104, 337-339.
32. (a) Ryu, J.-S.; Marks, T. J.; McDonald, F. E. J. Org. Chem. 2004, 69, 1038-1052.
33. (b) Gribkov, D. V.; Hampel, F.; Hultzsch, K. C. Eur. J. Inorg. Chem. 2004, 4091-4101.
34. (c) Kim, Y. K.; Livinghouse, T.; Horino, Y. J. Am. Chem. Soc. 2003, 125, 9560-9561.
35. (d) Ryu, J.-S.; McDonald, F. E.; Marks, T. J. Org. Lett. 2001, 3, 3091-3094.
36. (e) Kim, Y. K.; Livinghouse, T.; Bercaw, J. E. Tetrahedron Lett. 2001, 42, 2933-2935.
37. (f) Molander, G. A.; Dowdy, E. D. J. Org. Chem. 1999, 64, 6515-6517.
38. (g) Molander, G. A.; Dowdy, E. D. J. Org. Chem. 1998, 63, 8983-8988.
39. (a) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275-294.
40. (b) Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108-4109.
41. (c) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241-10254.
42. (d) O'Shaughnessy, P. N.; Knight, P. D.; Morton, C.; Gillespie, K. M.; Scott, P. Chem. Commun. 2003, 1770-1771.
43. (e) Kim, J. Y.; Livinghouse, T. Org. Lett. 2005, 7, 1737-1739.
44. (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1757-1771.
45. (b) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295-9306.
46. (c) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3370-3372.
47. (d) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708.
48. (e) Li, Y.; Fu, P.-F.; Marks, T. J. Organometallics 1994, 13, 439-440.
49. (a) Arredondo, V. M.; McDonald, F. E.; Marks, T. J. Organometallics 1999, 10, 1949-1960.
50. (b) Arredondo, V. M.; Tian, S.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1999, 121, 3633-3639.
51. (c) Arredondo, V. M.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 4871-4872.
52. (a) Hong, S.; Kawaoka, A. M.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 15878-15892.
53. (b) Hong, S.; Marks, T. J. J. Am. Chem. Soc. 2003, 124, 7886-7887.
54. Hydrophosphination: (a) Kawaoka, A.; Marks, T. J. J. Am. Chem. Soc. 2005, 127, 6311-6324.
55. (b) Kawaoka, A. M.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 12764-12765.
56. (c) Kawaoka, A. M.; Douglass, M. R.; Marks, T. J. Organometallics 2003, 22, 4030-4032.
57. (d) Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221-10238.
58. (e) Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824-1825.
59. Hydrophosphination mediated by Pd, Pt, and Ni complexes: (a) Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarnito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950-953.
60. (b) Wicht, D. K.; Kourkine, Kovacik, I.; Glueck, D. S.; Cancolina, T. E.; Yap, G. P. A.; Incarnito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381-5394.
61. (c) Costa, E.; Pringle, P. G.; Worboys, K. Chem. Comm. 1998, 49-50.
62. (d) Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039-5040.
63. (e) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571-1572.
64. (f) Using no transition-metal catalyst: Gaumont, A.-C.; Simon, A.; Denis, J.-M. Tetrahedron Lett. 1998, 39, 985-988.
65. (a) Quin, L. D.; Hughes, A. N. In The Chemistry of Organo-phosphorous Compounds; Hartley, F. R., Ed.; Wiley: Chichester, U.K., 1990; Vol 1, pp 295-394.
66. (b) Quin, L. D. In The Heterocyclic Chemistry of Phosphorus: Systems Based on the Phosphorus-Carbon Bond; Wiley: New York, 1981.
67. Dillon, K. B.; Mathey, F.; Nixon J. F. In Phosphorus: The Carbon Copy; Wiley: Chichester, U.K., 1998.
68. Price, N. R.; Chambers, J. In The Chemistry of Organophos-phorus Compounds; Hartley, F. R., Ed.; Wiley: Chichester, U.K., 1990; Vol 1, pp 643-661.
69. (a) Burk, M. J. Acc. Chem. Res. 2000, 33, 363-372.
70. (b) Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375-9376.
71. (c) Burk, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423-4424.
72. (d) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138.
73. Data from: (a) Nolan, S. P.; Stern, D.; Hdden, D.; Marks, T. J. ACS Symp. Ser. 1990, No. 428, 159-174.
74. (b) Nolan, S. P.; Stern, D.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 7844-7853.
75. (c) Skinner, H. A.; Pilcher, G. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: Chichester, U.K., 1982; Vol. 1, Chapter 2.
76. (d) Goldwhite, H. Introduction to Phosphorus Chemistry; Cambridge University Press: Cambridge, U.K., 1981.
77. (a) Luo, Y.; Selvam, P.; Koyama, M.; Kubo, M.; Miyamoto, A. Chem. Lett. 2004, 33, 780-785.
78. (b) Margl, P.; Deng, L.; Ziegler, T. Top. Catal. 1999, 7, 187-208.
79. (c) Perrin, L.; Maron, L.; Eisenstein, O.; Schwartz, D. J.; Burns, C. J.; Andersen, R. A. Organometallics 2003, 22, 5447-5453.
80. (d) Eisenstein, O.; Maron, L. J. Organomet. Chem. 2002, 647, 190-197.
81. (e) Margl, P.; Deng, L.; Ziegler, T. J. Am. Chem. Soc. 1999, 121, 154-162.
82. (f) Perrin, L.; Maron, L.; Eisenstein, O. New J. Chem. 2004, 28, 1255-1259.
83. (g) Perrin, L.; Maron, L.; Eisenstein, O. Inorg. Chem. 2002, 41, 4355-4362.
84. (h) Margl, P.; Deng, L.; Ziegler, T. J. Am. Chem. Soc. 1998, 120, 5517-5525.
85. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
86. (a) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261.
87. (b) Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654-3665.
88. Peng, C.; Schlegel, H. B. Isr. J. Chem. 1994, 33, 449-454.
89. (a) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161.
90. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
91. (a) Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239-245.
92. (b) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129.
93. (c) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327-335.
94. (d) Cances, M. T.; Mennucci, V.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032-3041.
95. (e) Barone, V.; Cossi, M.; Tomasi; J. J. Comput. Chem. 1998, 19, 404-417.
96. Frisch, M. J., et al. Gaussian 03, Revision A.1; Gaussian, Inc., Pittsburgh, PA, 2003.
97. See: R. F.; Dutoi, A. D.; McConnell, K. W.; Naylor R. M. J. Am. Chem. Soc. 2001, 123, 2839-2848.
98. Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091-8103.
99. (a) Pearson, R. G. J. Chem. Educ. 1987, 64, 561-567.
100. (b) Ho, T.-L. Hard and Soft Acids and Base Principles in Organic Chemistry; Academic Press: New York, 1997.
101. (c) Pearson, R. G. Hard and Soft Acids and Bases; Dowden, Hutchinson, and Ross, Inc.: Straudsburg, 1973.
102. Motta, A.; Lanza, G.; Fragalà, I. L.; Marks, T. J. Organometallics 2004, 23, 4097-4104.