Intramolecular nitrile C-H bond activation in nickel NHC complexes: A route to new nickelacycles

Organometallics

Volumn 30, Issue 12, 2011, Pages 3400-3411

  Oertel, Anna Magdalena ^a   Freudenreich, Julien ^a   Gein, Jordan ^a   Ritleng, Vincent ^a   Veiros, Luis F ^b   Chetcuti, Michael J ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC CARBONS; C-H ACTIVATION; C-H BOND; CATIONIC COMPLEXES; CATIONIC COMPOUNDS; CH-BOND ACTIVATION; CYCLOPENTADIENYLS; DFT STUDY; DIRECT REACTIONS; GOOD YIELD; IMIDAZOLIUM SALT; MECHANISM OF FORMATION; METALLACYCLES; N-HETEROCYCLIC CARBENES; NEUTRAL COMPLEXES; NICKEL COMPLEX; NICKELACYCLES; NICKELOCENE; NITRILE GROUPS; NITROGEN ATOM; ROOM TEMPERATURE; SIDE-CHAINS; SINGLE CRYSTAL X-RAY CRYSTALLOGRAPHY; SINGLE CRYSTAL X-RAY DIFFRACTION; SPECTROSCOPIC TECHNIQUE; STRUCTURAL STUDIES;

ACETONITRILE; ACTIVATION ANALYSIS; CYANIDES; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

X RAY CRYSTALLOGRAPHY;

EID: 79959406755     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200246k     Document Type: Article

References (103)

1. Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361
2. Poyatos, M.; Mata, J. A.; Peris, E. Chem. Rev. 2009, 109, 3677
3. Díez-González, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612
4. Arnold, P. L.; Casely, I. J. Chem. Rev. 2009, 109, 3599
5. Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122
6. Gade, L. H.; Bellemin-Laponnaz, S. Coord. Chem. Rev. 2007, 251, 718
7. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290
8. Díez-González, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874
9. Cavallo, L.; Correa, A.; Costabile, C.; Jacobsen, H. J. Organomet. Chem. 2005, 690, 5407
10. Strassner, T. Top. Organomet. Chem. 2004, 13, 1
11. Jacobsen, H.; Correa, A.; Poater, A.; Costabile, C.; Cavallo, L. Coord. Chem. Rev. 2009, 253, 687
12. Radius, U.; Bickelhaupt, F. M. Coord. Chem. Rev. 2009, 253, 678
13. Frenkin, G.; Solà, M.; Vyboishchikov, S. F. J. Organomet. Chem. 2005, 690, 6178
14. Herrmann, W. A.; Elison, M.; Fischer, J.; Kocher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2371
15. Tucker, C. E.; de Vries, J. G. Top. Catal. 2002, 19, 111
16. For Suzuki couplings, see for example: Ritleng, V.; Oertel, A. M.; Chetcuti, M. J. Dalton Trans. 2010, 39, 8153
17. Kuroda, J.-I.; Inamoto, K.; Hiroya, K.; Doi, T. Eur. J. Org. Chem. 2009, 2251
18. Zhou, Y.; Xi, Z.; Chen, W.; Wang, D. Organometallics 2008, 27, 5911
19. Lee, C.-C.; Ke, W.-C.; Chan, K.-T.; Lai, C.-L.; Hu, C.-H.; Lee, H. M. Chem. Eur. J. 2007, 13, 582
20. McGuinness, D. S.; Cavell, K. J.; Skelton, B. W.; White, A. H. Organometallics 1999, 18, 1596
21. For Kumada couplings, see for example: Berding, J.; Lutz, M.; Spek, A. L.; Bouwman, E. Organometallics 2009, 28, 1845
22. Gu, S.; Chen, W. Organometallics 2009, 28, 909
23. Xi, Z.; Liu, B.; Chen, W. J. Org. Chem. 2008, 73, 3954
24. Matsubara, K.; Ueno, K.; Shibata, Y. Organometallics 2006, 25, 3422
25. For examples of Negishi coupling, see: Zhang, C.; Wang, Z.-X. Organometallics 2009, 28, 6507
26. Xi, Z.; Zhou, Y.; Chen, W. J. Org. Chem. 2008, 73, 8497
27. For cross-couplings of fluorinated arenes, see: Schaub, T.; Backes, M.; Radius, U. J. Am. Chem. Soc. 2006, 128, 15964
28. Böhm, V. P. W.; Gstöttmayr, C. W. K.; Weskamp, T.; Herrmann, W. A. Angew. Chem., Int. Ed. 2001, 40, 3387
29. See for examples: Matsubara, K.; Ueno, K.; Koga, Y.; Hara, K. J. Org. Chem. 2007, 72, 5069
30. Kelly, R. A., III; Scott, N. M.; Díez-González, S.; Stevens, E. D.; Nolan, S. P. Organometallics 2005, 24, 3442
31. Desmarets, C.; Schneider, R.; Fort, Y. J. Org. Chem. 2002, 67, 3029
32. See for examples: Tekavec, T. N.; Louie, J. J. Org. Chem. 2008, 73, 2641
33. McCormick, M. M.; Duong, H. A.; Zuo, G.; Louie, J. J. Am. Chem. Soc. 2005, 127, 5030
34. Duong, H. A.; Cross, M. J.; Louie, J. J. Am. Chem. Soc. 2004, 126, 11438
35. Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N. J. Am. Chem. Soc. 2002, 124, 15188
36. Dible, B. R.; Sigman, M. S. J. Am. Chem. Soc. 2003, 125, 872
37. Lee, C. H.; Laitar, D. S.; Mueller, P.; Sadighi, J. P. J. Am. Chem. Soc. 2007, 129, 13802
38. Schaub, T.; Backes, M.; Radius, U. Chem. Commun. 2007, 2037
39. Schaub, T.; Döring, C.; Radius, U. Dalton Trans. 2007, 1993
40. Oertel, A. M.; Ritleng, V.; Chetcuti, M. J.; Veiros, L. F. J. Am. Chem. Soc. 2010, 132, 13588
41. For C-H activations by cyclonickelation, see: Kleiman, J. P.; Dubeck, M. J. Am. Chem. Soc. 1963, 85, 1544
42. Ustynyuk, Y. A.; Barinov, I. V. J. Organomet. Chem. 1970, 23, 551
43. Moulton, C. J.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1976, 1020
44. Rimml, H.; Venanzi, L. M. J. Organomet. Chem. 1983, 259, C6
45. Pattanayak, P.; Pratihar, J. L.; Patra, D.; Burrows, A.; Mohan, M.; Chattopadhyay, S. Eur. J. Inorg. Chem. 2007, 4263
46. Volpe, E. C.; Chadeayne, A. R.; Wolczanski, P. T.; Lobkovsky, E. B. J. Organomet. Chem. 2007, 692, 4774
47. Piro, N. A.; Owen, J. S.; Bercaw, J. E. Polyhedron 2004, 23, 2797
48. For intermolecular C-H activations, see: Clement, N. D.; Cavell, K. J.; Jones, C.; Elsevier, C. J. Angew. Chem., Int. Ed. 2004, 43, 1277
49. Liang, L.-C.; Chien, P.-S.; Huang, Y.-L. J. Am. Chem. Soc. 2006, 128, 15562
50. Huynh, H. V.; Wu, J. J. Organomet. Chem. 2009, 694, 323
51. Fürstner, A.; Krause, H.; Ackermann, L.; Lehmann, C. W. Chem. Commun. 2001, 2240
52. Dyson, P. J.; Zhao, D.; Fei, Z. WO 2005019185 A1, 2005.
53. Zhao, D.; Fei, Z.; Scopelliti, R.; Dyson, P. J. Inorg. Chem. 2004, 43, 2197
54. Oertel, A. M.; Ritleng, V.; Chetcuti, M. J. Synthesis 2009, 1647
55. Ritleng, V.; Barth, C.; Brenner, E.; Milosevic, S.; Chetcuti, M. J. Organometallics 2008, 27, 4223
56. Abernethy, C. D.; Cowley, A. H.; Jones, R. A. J. Organomet. Chem. 2000, 596, 3
57. Kelly, R. A.; Scott, N. M.; Díez-González, S.; Stevens, E. D.; Nolan, S. P. Organometallics 2005, 24, 3442
58. Ritleng, V.; Brenner, E.; Chetcuti, M. J. J. Chem. Educ. 2008, 85, 1646
59. Smith, M. E.; Andersen, R. A. J. Am. Chem. Soc. 1996, 118, 11119
60. Holland, P. L.; Smith, M. E.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 12815
61. Carmona, C. C.; Clapham, S.; Gonidec, M.; Ritleng, V.; Braunstein, P.; Welter, R.; Chetcuti, M. J. Eur. J. Inorg. Chem. 2010, 403
62. Wickenden, A. E.; Krause, R. A. Inorg. Chem. 1965, 4, 404
63. No ν(CN) stretches were detected in the IR spectra of various samples of complex 2d.
64. Ryabov, A. D. Chem. Rev. 1990, 90, 403
65. Complex 3d was not fully characterized, because its formation is sluggish and it could only be obtained pure once in very low yield.
66. Demerseman, B.; Mbaye, M. D.; Sémeril, D.; Toupet, L.; Bruneau, C.; Dixneuf, P. H. Eur. J. Inorg. Chem. 2006, 1174
67. For interesting studies concerning the oxidative addition of the α-C-H bond of cyanoalkyls on related Rh species, see: Evans, M. E.; Li, T.; Jones, W. D. J. Am. Chem. Soc. 2010, 132, 16278
68. Evans, M. E.; Li, T.; Vetter, A. J.; Rieth, R. D.; Jones, W. D. J. Org. Chem. 2009, 74, 6907
69. Macaev, F.; Gavrilov, K.; Muntyanu, V.; Styngach, E.; Vlad, L.; Bets, L.; Pogrebnoi, S.; Barba, A. Chem. Natur. Comp. 2007, 43, 136
70. Occhipinti, G.; Bjørsvik, H.-R.; Törnroos, K. W.; Fürstner, A.; Jensen, V. R. Organometallics 2007, 26, 4383
71. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112
72. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7
73. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc., Wallingford, CT, 2004.
74. Hehre, W. J.; Radom, L.; Schleyer, P. v.R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
75. Parr, R. G.; Yang, W. In Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
76. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1997, 78, 1396
77. Perdew, J. P. Phys. Rev. B 1986, 33, 8822
78. Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; Vol. 3, p 1.
79. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270
80. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284
81. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 2299
82. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111
83. Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724
84. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257
85. Hariharan, P. C.; Pople, J. A. Mol. Phys. 1974, 27, 209
86. Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163
87. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213
88. Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49
89. Peng, C.; Schlegel, H. B. Isr. J. Chem. 1994, 33, 449
90. McClean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639
91. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650
92. Wachters, A. J. H. J. Chem. Phys. 1970, 52, 1033
93. Hay, P. J. J. Chem. Phys. 1977, 66, 4377
94. Raghavachari, K.; Trucks, G. W. J. Chem. Phys. 1989, 91, 1062
95. Binning, R. C., Jr.; Curtiss, L. A. J. Comput. Chem. 1990, 11, 1206
96. McGrath, M. P.; Radom, L. J. Chem. Phys. 1991, 94, 511
97. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294
98. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265
99. Cancès, M. T.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032
100. Cossi, M.; Barone, V.; Mennucci, B.; Tomasi, J. Chem. Phys. Lett. 1998, 286, 253
101. Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, 5151
102. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999
103. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43