Metal carbenes in homogeneous alkene metathesis: Computational investigations

Journal of Organometallic Chemistry

Volumn 738, Issue , 2013, Pages 76-91

  Du Toit, J I ^a   Van Sittert, C G C E ^a   Vosloo, H C M ^a  

^a NORTH WEST UNIVERSITY   (South Africa)

Author keywords

Metathesis; Molecular modeling; Transition metal carbene complexes

Indexed keywords

ALKENE METATHESIS; CARBENES; COMPUTATIONAL INVESTIGATION; COMPUTATIONAL STUDIES; METAL CARBENES; METAL-CARBENE COMPLEXES; METATHESIS; THEORETICAL TREATMENTS;

METAL COMPLEXES; MOLECULAR MODELING; TRANSITION METAL COMPOUNDS;

HYDROCARBONS;

EID: 84877678830     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2013.03.041     Document Type: Review

References (106)

1. R.H. Crabtree The Organometallic Chemistry of the Transition Elements fourth ed. 2005 Wiley New York
2. A.M. Rouhi Chem. Eng. News (Washington) 80 2002 34
3. J.C. Mol J. Mol. Catal. A 213 2004 39
4. C.P. Casey, and T.J. Burkhardt J. Am. Chem. Soc. 96 1974 7808
5. T.J. Katz, and J. McGinnis J. Am. Chem. Soc. 97 1975 1592
6. T.J. Katz, J. McGinnis, and S. Hurwitz J. Am. Chem. Soc. 98 1976 605
7. R.R. Schrock, J.S. Murdzek, G.C. Bazan, J. Robbins, M. DiMare, and M. O'Regan J. Am. Chem. Soc. 112 1990 3875
8. S.T. Nguyen, L.K. Johnson, and R.H. Grubbs J. Am. Chem. Soc. 114 1992 3974
9. N. Calderon, H.Y. Chen, and K.W. Scott Tetrahedron Lett. 34 1967 3327
10. Y. Chauvin, and J. Herisson Makromol. Chem. 141 1971 161
11. R.R. Schrock, S. Rocklage, J. Wengrovious, G. Rupprecht, and J. Fellmann J. Mol. Catal. 8 1980 73
12. J.P. Morgan, and R.H. Grubbs Org. Lett. 2 2000 3153
13. C. Adlhart, and P. Chen Angew. Chem. Int. Ed. 41 2002 4484
14. S.H. Hong, and R.H. Grubbs J. Am. Chem. Soc. 128 2006 3508
15. T. Ritter, A. Hejl, A.G. Wenzel, T.W. Funk, and R.H. Grubbs Organometallics 25 2006 5740
16. M. Jordaan, P. Van Helden, C.G.C.E. Van Sittert, and H.C.M. Vosloo J. Mol. Catal. A 254 2006 145
17. M. Jordaan, and H.C.M. Vosloo Adv. Synth. Catal. 349 2007 184
18. S.J. Malcolmson, S.J. Meek, E.S. Sattely, R.R. Schrock, and A.H. Hoveyda Nature 456 2008 933
19. F.T.I. Marx, J.H.L. Jordaan, and H.C.M. Vosloo J. Mol. Model. 15 2009 1371
20. I. Ibrahem, M. Yu, R.R. Schrock, and A.H. Hoveyda J. Am. Chem. Soc. 131 2009 3844
21. K. Endo, and R.H. Grubbs J. Am. Chem. Soc. 133 2011 8525
22. R.H. Grubbs, T.M. Trnka, and M.S. Sanforf Transition Metal-Carbene Complexes in Olefin Metathesis and Related Reactions H. Kurosawa, A. Yamamoto, Current Methods in Inorganic Chemistry: Fundamentals of Molecular Catalysis vol. 3 2003 Elsevier Amsterdam
23. G. Occhipinti, and V.R. Jensen Organometallics 30 2011 3522
24. T.E. Taylor, and M.B. Hall J. Am. Chem. Soc. 106 1984 1576
25. F.Z. Dörwald Metal Carbenes in Organic Synthesis 1999 Wiley-VCH Weinheim
26. F. Mathey, and A. Sevin Molecular Chemistry of the Transition Elements - An Introductory Course 1996 Wiley Chichester
27. R.R. Schrock J. Am. Chem. Soc. 96 1974 6796
28. E.O. Fischer, and A. Maasböl Angew. Chem. Int. Ed. Engl. 3 1964 580
29. J.C. Garrison, and W.J. Youngs Chem. Rev. 105 2005 3978
30. S. Kotha, and M.K. Dipak Tetrahedron 68 2012 397
31. S.F. Vyboishchikov, and G. Frenking Chem. Eur. J. 4 1998 1428
32. J. Ushio, H. Nakatsuji, and T. Yonezawa J. Am. Chem. Soc. 106 1984 5892
33. G.O. Spessard, and G.L. Miessler Organometallic Chemistry 1997 Prentice-Hall
34. M. Tlenkopatchev, and S. Fomine J. Organomet. Chem. 630 2001 157
35. O. Eisenstein, and R. Hoffman J. Am. Chem. Soc. 103 1981 5582
36. T.H. Upton, and A.K. Rappé J. Am. Chem. Soc. 107 1985 1206
37. A.K. Rappé, and W.A. Goddard III J. Am. Chem. Soc. 104 1982 297
38. F.U. Axe, and J.W. Andzelm J. Am. Chem. Soc. 121 1999 5396
39. S.F. Vyboishchikov, M. Bühl, and W. Thiel Chem. Eur. J. 8 2002 3962
40. S. Fomine, S.M. Vargas, and M.A. Tlenkopatchev Organometallics 22 2003 93
41. F. Bernardi, A. Bottoni, and G.P. Miscione Organometallics 22 2003 940
42. L. Cavallo J. Am. Chem. Soc. 124 2002 8965
43. C. Costabile, and L. Cavallo J. Am. Chem. Soc. 126 2004 9592
44. D. Benitez, E. Tkatchouk, and W.A. Goddard III Chem. Commun. 2008 6194
45. W. Janse van Rensburg, P.J. Steynberg, W.H. Meyer, M.M. Kirk, and G.S. Forman J. Am. Chem. Soc. 126 2004 14332
46. C. Adlhart, and P. Chen J. Am. Chem. Soc. 126 2004 3496
47. C.H. Suresh, and N. Koga Organometallics 23 2004 76
48. O.M. Aagaard, R.J. Meier, and F. Buda J. Am. Chem. Soc. 120 1998 7174
49. B.F. Straub Angew. Chem. Int. Ed. 44 2005 5974
50. M. Vyboishchikov, and W. Thiel Chem. Eur. J. 11 2005 3921
51. A.C. Tsipis, A.G. Orpen, and J.N. Harvey Dalton Trans. 2005 2849
52. A. Correa, and L. Cavallo J. Am. Chem. Soc. 128 2006 13352
53. G. Occhipinti, H. Bjørsvik, and V.R. Jensen J. Am. Chem. Soc. 128 2006 6952
54. K.B. Wiberg Tetrahedron 24 1968 1083
55. W. Janse van Rensburg, P.J. Steynberg, M.M. Kirk, W.H. Meyer, and G.S. Forman J. Organomet. Chem. 691 2006 5312
56. B.F. Straub Adv. Synth. Catal. 349 2007 204
57. E.L. Dias, S.T. Nguyen, and R.H. Grubbs J. Am. Chem. Soc. 119 1997 3887
58. S. Naumov, and M.R. Buchmeiser J. Phys. Org. Chem. 21 2008 963
59. P.E. Romero, and W.E. Piers J. Am. Chem. Soc. 129 2007 1698
60. C.E. Webster J. Am. Chem. Soc. 129 2007 7490
61. K. Getty, M.U. Delgado-Jaime, and P. Kennepohl J. Am. Chem. Soc. 129 2007 15774
62. A. Poater, F. Ragone, A. Correa, and L. Cavallo J. Am. Chem. Soc. 131 2009 9000
63. T. Weskamp, F.J. Kohl, W. Hieringer, D. Gleich, and W.A. Herrman Angew. Chem. Int. Ed. 38 1999 2416
64. R.J. Meier, O.M. Aagaard, and F. Buda J. Mol. Catal. A 160 2000 189
65. H. Jacobsen Dalton Trans. 2006 2214
66. W.W. Schoeller, D. Schroeder, and A.B. Rozhenko J. Organomet. Chem. 690 2005 6079
67. R.L. Lord, H. Wang, M. Vieweger, and M. Baik J. Organomet. Chem. 691 2006 5505
68. I. Fernández, N. Lugan, and G. Lavigne Organometallics 31 2012 1155
69. P. Van der Gryp, S. Marx, and H.C.M. Vosloo J. Mol. Catal. A 355 2012 85
70. F. Nuñez-Zarur, J. Poater, L. Rodríguez-Santiago, X. Solans-Monfort, M. Solà, and M. Sodupe Comput. Theor. Chem. 996 2012 57
71. F. Nunñez-Zarur, X. Solans-Monfort, L. Rodriguez-Santiago, and M. Sodupe Organometallics 31 2012 4203
72. I.W. Ashworth, I.H. Hillier, D.J. Nelson, J.M. Percy, and M.A. Vincent Chem. Commun. 47 2011 5428
73. M.J. Lee, K.Y. Lee, J.Y. Lee, and J.N. Kim Org. Lett. 6 2004 3313
74. S. Fomine, and M. Tlenkopatchev J. Organomet. Chem. 691 2006 5189
75. I.H. Hillier, S. Pandian, J.M. Percy, and M.A. Vincent Dalton Trans. 40 2011 1061
76. K.A. Burdett, L.D. Harris, P. Margl, B.R. Maughon, T. Mokhtar-Zadeh, P.C. Saucier, and E.P. Wasserman Organometallics 23 2004 2027
77. S. Fomine, J.V. Ortega, and M.A. Tlenkopatchev J. Mol. Catal. A 236 2005 156
78. S. Fomine, J.V. Ortega, and M.A. Tlenkopatchev Organometallics 24 2005 5696
79. S. Fomine, J.V. Ortega, and M.A. Tlenkopatchev J. Organomet. Chem. 691 2006 3343
80. S. Fomine, J.V. Ortega, and M.A. Tlenkopatchev J. Mol. Catal. A 263 2007 121
81. S. Fomine, S. Gutierrez, and M.A. Tlenkopatchev J. Organomet. Chem. 694 2009 3287
82. Y. Lu, F. Tournilhac, L. Leibler, and Z. Guan J. Am. Chem. Soc. 134 2012 8424
83. S. Fomine, and M.A. Tlenkopatchev J. Organomet. Chem. 701 2012 68
84. W.A. Goddard III, and D. Benitez J. Am. Chem. Soc. 127 2005 12218
85. C. Adlhart, C. Hinderling, H. Baumann, and P. Chen J. Am. Chem. Soc. 122 2000 8204
86. P. Hofmann, M.A.O. Volland, S.M. Hansen, F. Eisenträger, J.H. Gross, and K. Stengel J. Organomet. Chem. 66 2000 88
87. J.N. Coalter, J.C. Bollinger, J.C. Huffman, U. Werner-Zwanziger, K.G. Caulton, E.R. Davidson, H. Gérard, E. Clot, and O. Eisenstein New J. Chem. 24 2000 9
88. M. Jordaan, and H.C.M. Vosloo Mol. Simul. 34 2008 997
89. I.C. Stewart, D. Benitez, D.J. O'Leary, E. Tkatchouk, M.W. Day, W.A. Goddard III, and R.H. Grubbs J. Am. Chem. Soc. 131 2009 1931
90. X. Solans-Monfort, R. Pleixats, and M. Sodupe Chem. Eur. J. 16 2010 7331
91. A. Fedorov, L. Batiste, A. Bach, D.M. Birney, and P. Chen J. Am. Chem. Soc. 133 2011 12162
92. I.T. Sabbagh, and P.T. Kaye J. Mol. Struct.: THEOCHEM 763 2006 37
93. T.P.M. Goumans, A.W. Ehlers, and K. Lammertsma Organometallics 24 2005 3200
94. A. Poater, X. Solans-Monfort, E. Clot, C. Copéret, and O. Eisenstein J. Am. Chem. Soc. 129 2007 8207
95. X. Solans-Monfort, E. Clot, C. Copéret, and O. Eisenstein J. Am. Chem. Soc. 127 2005 14015
96. M. Vasiliu, S. Li, A.J. Arduengo III, and D.A. Dixon J. Phys. Chem. C 115 2011 12106
97. T.R. Cundari, and M.S. Gordon Organometallics 11 1992 55
98. E. Folga, and T. Ziegler Organometallics 12 1993 325
99. H.H. Fox, M.H. Schofield, and R.R. Schrock Organometallics 13 1994 2804
100. Y. Wu, and Z. Peng J. Am. Chem. Soc. 119 1997 8043
101. Y. Wu, and Z. Peng Inorg. Chim. Acta 345 2003 241
102. K. Monteyne, and T. Ziegler Organometallics 17 1998 5901
103. A.K. Rappé, and W.A. Goddard III J. Am. Chem. Soc. 102 1980 5114
104. A.K. Rappé, and W.A. Goddard III J. Am. Chem. Soc. 104 1982 448
105. T.R. Cundari, and M.S. Gordon J. Am. Chem. Soc. 113 1991 5231
106. T.R. Cundari J. Am. Chem. Soc. 114 1992 7879