Design of sterically demanding, electron-rich carbene ligands with the perimidine scaffold

Organometallics

Volumn 26, Issue 11, 2007, Pages 2885-2895

  Bazinet, Patrick ^a   Ong, Tiow Gan ^a   O'Brien, Julie S ^a   Lavoie, Nathalie ^a   Bell, Eleanor ^a   Yap, Glenn P A ^b   Korobkov, Ilia ^a   Richeson, Darrin S ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; ELECTRON-DONATING ABILITY; ENETETRAMINES; PERIMIDINE SCAFFOLD;

DEPROTONATION; ELECTRONIC STRUCTURE; LIGANDS; METAL COMPLEXES; REACTION KINETICS; SPECTROSCOPIC ANALYSIS;

ORGANOMETALLICS;

EID: 34249947919     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0701827     Document Type: Article

References (56)

1. Arduengo, A. J., III; Harlow, R. L; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
2. Carbene Chemistry: from fleeting intermediates to powerful reagents; Bertrand, G., Ed.; Marcel Dekker: New York, 2002.
3. For reviews see: (a) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
4. (b) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1291.
5. (c) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. 1997, 36, 2162.
6. Jafarpour, L.; Nolan, S. P. J. Organomet. Chem. 2001, 677, 17.
7. Denk, K.; Sirsch, P.; Herrmann, W. A. J. Organomet. Chem. 2002, 649, 219.
8. Weskamp, T.; Kohl, F. J.; Hieringer, W.; Gleich, D.; Herrmann, W. A. Angew. Chem., Int. Ed. 1999, 38, 2416.
9. Huang, J.; Jafarpour, L.; Hillier, A. C.; Stevens, E. D.; Nolan, S. P. Organometallics 2001, 20, 2878.
10. Chianese, A. R.; Li, X.; Janzen, M. C.; Faller, J. W.; Crabtree, R. H. Organometallics 2003, 22, 1663.
11. Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370.
12. Principles and Applications of Organotransition Metal Chemistry, 2nd ed.; Collman, J. P., Hedegus, L. S., Norton, J. R., Finke, R. G., Eds.; University Science: Mill Valley, CA, 1987.
13. Homogeneous Catalysis with Metal Phosphine Complexes; Pignolet, L. H., Ed.; Plenum: New York, 1983.
14. Parshall, G. W.; Ittel, S. Homogeneous Catalysis; John Wiley & Sons: New York 1992.
15. (a) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023.
16. (b) Boehme, C.; Frenking, G. J. Am. Chem. Soc. 1996, 118, 2039.
17. Bazinet, P.; Yap, G. P. A.; Richeson, D. S. J. Am. Chem. Soc. 2003, 125, 13314.
18. Yun, J.; Marinez, E. R.; Grubbs, R. H. Organometallics 2004, 23, 4172.
19. Six-membered ring carbene are reported in: (a) Guillen, F.; Winn, C. L.; Alexakis, A. Tetrahedron: Asymmetry 2001, 12, 2083.
20. (b) Alder, R. W.; Blake, M. E.; Bortolotti, C.; Bufali, S.; Butts, C. P.; Linehan, E.; Oliva, J. M.; Orpen, A. G.; Quayle, M. J. Chem. Commun. 1999, 241.
21. For reports of annelated carbenes see: (a) Hahn, F. E.; Wittenbecher, L.; Le Van, D.; Fröhlich, R. Angew. Chem., Int. Ed. 2000, 39, 541.
22. (b) Liu, Y.; Lindner, P. E.; Lemal, D. M. J. Am. Chem. Soc. 1999, 121, 10626.
23. Despagnet-Ayoub, E.; Grubbs, R. H. J. Am. Chem. Soc. 2004, 126, 10198.
24. Alder, R. W.; Chaker, L.; Paolini, F. P. V. Chem. Commun. 2004, 2172.
25. Scarborough, C. C.; Grady, M. J. W.; Guzei, I. A.; Gandhi, B. A. Stahl, S. S. Angew. Chem., Int. Ed. 2005, 44, 5269.
26. Scarborough, C. C.; Popp, B. V.; Guzei, I. A.; Stahl, S. S. J. Organomet. Chem. 2005, 690, 6143.
27. Handbook of Heterocyclic Chemistry, 2nd ed.; Katritzky, A. R., Pozharskii, A. F., Eds.; Pergamon: New York, 2000.
28. Details for the characterization of 9 can be found in the Supporting Information.
29. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
30. 13C shifts for typical carbenes see: Herrmann, W. A.; Öfele, K.; Preysing, D. v.; Herdtweck, E. J. Organomet. Chem. 2003, 684, 235.
31. A summary of crystallographic details and tables of selected bond distance and angles are provided in the Supporting Information.
32. Arduengo, A. J.; Goerlich, J. R.; Marshall, W. J. J. Am. Chem. Soc. 1995, 117, 11027.
33. Denk, M. K.; Thadani, A.; Hatano, K.; Lough, A. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2607.
34. The dimerization of N-stabilized carbenes has recently been reviewed in: (a) Alder, R. W.; Blake, M. E.; Chaker, L.; Harvey, J. N.; Paolini, F.; Schutz, J. Angew. Chem., Int. Ed. 2004, 43, 5896.
35. (b) Graham, D. C.; Cavel, K. J.; Yates, B. F. J. Phys. Org. Chem. 2005, 18, 298.
36. Cetinkaya, E.; Hitchcock, P. B.; Jasim, H. A.; Lappert, M. F.; Spyropoulos, K. J. Chem. Soc., Perkin Trans. 1 1992, 561.
37. Dynamic dimerization of benzimidazole carbenes has been recently reported: Kamplain, J. W.; Bielawski, C. W. Chem. Commun. 2006, 1727.
38. Taton, T. A.; Chen, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1011.
39. Hahn, F. E.; Paas, M.; Le Van, D.; Lügger, T. Angew. Chem., Int. Ed. 2003, 42, 5243.
40. Dixon, D. A.; Arduengo, A. J., III. J. Phys. Chem. 1991, 95, 4180.
41. Heinemann, C.; Thiel, W. Chem. Phys. Lett. 1994, 217, 11.
42. Cheng, M. J.; Hu, C. H. Chem. Phys. Lett. 2001, 349, 477.
43. Carter, E. A.; Goddard, W. A., III. J. Phys. Chem. 1986, 90, 998.
44. Frisch, M. J., et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
45. Hermann, W. A.; Köcher, C.; Goossen, L. K.; Artus, G. R. J. Chem. Eur. J. 1996, 2, 1627.
46. Enders, D.; Gielen, H. J. Organomet. Chem. 2001, 617, 70.
47. Doyle, M. J.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1974, 679.
48. The cif file for 20 can be found in the Supporting Information.
49. For reviews on the use of enetetramines in the synthesis of metalcarbene complexes see: Lappert, M. F. J. Organomet. Chem. 2005, 690, 5467.
50. Lappert, M. F. J. Organomet. Chem. 1988, 358, 185.
51. Cavallo, L.; Correa, A.; Costabile. C.; Jacobsen, H. J. Organomet. Chem. 2005, 690, 5407.
52. Scott, N. M.; Nolan, S. P. Eur. J. Inorg. Chem. 2005, 1815.
53. Dorta, R.; Stevens, E. D.; Scott, N. M.; Costabile, C.; Cavallo, L.; Hoff, C. D.; Nolan, S. P. J. Am. Chem. Soc. 2005, 127, 2485.
54. Hillier, A. C.; Sommer, W. J.; Yong, B. S.; Peterson, J. L.; Cavallo, L.; Nolan, S. P. Organometallics 2003, 22, 4322.
55. Optimizations were carried out using the B3LYP functional and the LANL2DZ basis set with the Gaussian 03 program. The optimization results are provided in the Supporting Information.
56. Doyle, M. J.; Lappert, M. F.; Pye, P. L.; Terreros, P. J. Chem. Soc., Dalton Trans. 1984, 2355.