Computational studies of reactions of insertion of rhodium(I) and iridium(I) into N-H, N-CH3, and NCH2-H bonds of the diarylamine-based PNP pincer ligands

Organometallics

Volumn 30, Issue 11, 2011, Pages 2972-2979

  Surawatanawong, Panida ^b   Ozerov, Oleg V ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b Mahidol University   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC RINGS; CARBENES; COMPUTATIONAL STUDIES; DFT CALCULATION; DFT METHOD; DOMINANT MECHANISM; EXPERIMENTAL VALUES; H-BONDS; HIGH ENERGY; LIGAND SYSTEM; OXIDATIVE ADDITIONS; PINCER LIGANDS; SECONDARY AMINES;

IRIDIUM; LIGANDS; RHODIUM COMPOUNDS;

RHODIUM;

EID: 79958135935     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200020b     Document Type: Article

References (51)

1. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 5th ed.; Wiley-Interscience: New York, 2009; pp 153-164.
2. Hartwig, J. F. Organotransition Metal Chemistry: From Bonding to Catalysis; University Science Books: Sausalito, CA, 2009; pp 261-320.
3. Jones, W. D. Acc. Chem. Res. 2003, 36, 140.
4. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 5th ed.; Wiley-Interscience: New York, 2009; pp 164-169.
5. Hartwig, J. F. Organotransition Metal Chemistry: From Bonding to Catalysis; University Science Books: Sausalito, CA, 2009; pp 321-348.
6. Hartwig, J. F. Synlett 1997, 329.
7. Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
8. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
9. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
10. Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000; p 195.
11. Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2001, 219, 131.
12. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534-1544.
13. Surry, D. S.; Buchwald, S. L. Chem. Sci. 2010, Advance Article, DOI: 10.1039/ C0SC00331J.
14. Hartwig, J. F. Organotransition Metal Chemistry: From Bonding to Catalysis; University Science Books: Sausalito, CA, 2009; pp 907-913.
15. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1.
16. Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689.
17. Hartwig, J. F. Organotransition Metal Chemistry: From Bonding to Catalysis; University Science Books: Sausalito, CA, 2009; pp 967-983.
18. Takano, K.; Inagaki, A.; Akita, M. Chem. Lett. 2006, 35, 434.
19. Lin, B. L.; Clough, C. R.; Hillhouse, G. L. J. Am. Chem. Soc. 2002, 124, 2890.
20. Torrent, M.; Musaev, D. G.; Morokuma, K. Organometallics 2000, 19, 4402.
21. Tayebani, M.; Gambarotta, S.; Yap, G. Organometallics 1998, 17, 3639.
22. Bonanno, J. B.; Henry, T. P.; Neithamer, D. R.; Wolczanski, P. T.; Lobkovsky, E. B. J. Am. Chem. Soc. 1996, 118, 5132.
23. Chan, Y. W.; Renner, M. W.; Balch, A. L. Organometallics 1983, 2, 1888.
24. Gandelman, M.; Milstein, D. Chem. Commun. 2000, 1603.
25. Guibe, F. Tetrahedron 1998, 54, 2967.
26. Aresta, M.; Quaranta, E.; Dibenedetto, A.; Giannoccaro, P.; Tommasi, I.; Lanfranchi, M.; Tiripicchio, A. Organometallics 1997, 16, 834.
27. Erhardt, S.; Grushin, V. V.; Kilpatrick, A. H.; Macgregor, S. A.; Marshall, W. J.; Roe, D. C. J. Am. Chem. Soc. 2008, 130, 4828.
28. Ozerov, O. V.; Guo, C.; Fan, L.; Foxman, B. M. Organometallics 2004, 23, 5573.
29. Ozerov, O. V.; Guo, C.; Papkov, V. A.; Foxman, B. M. J. Am. Chem. Soc. 2004, 126, 4792.
30. Weng, W.; Guo, C.; Moura, C. P.; Yang, L.; Foxman, B. M.; Ozerov, O. V. Organometallics 2005, 24, 3487.
31. 2 groups.
32. Instead, with the "untied" ligand, the initial transformation was the displacement of chloride by the neutral tridentate PN(Me)P ligand to give [(PN(Me)P)Ir(COD)]+.
33. 2 intermediate (ΔG = 23.3 kcal/mol), but these were still too high to be accessible under mild experimental conditions.
34. Choi, J.; Choliy, Y.; Zhang, X.; Emge, T. J.; Krogh-Jespersen, K.; Goldman, A. S. J. Am. Chem. Soc. 2009, 131, 15627.
35. Wu, H.; Hall, M. B. Dalton Trans. 2009, 5933.
36. For examples of lengthening of theM-P bonds upon oxidation of the metal, see:Dunne, B. J.; Morris, R. B.; Orpen, A. G. J. Chem. Soc., Dalton Trans. 1991, 653.
37. Orpen, A. G.; Connelly, N. G. Organometallics 1990, 9, 1206.
38. Harlow, R. L.; McKinney, R. J.; Whitney, J. F. Organometallics 1983, 2, 1839.
39. Spivak, G. J.; Coalter, J. N.; Oliván, M.; Eisenstein, O.; Caulton, K. G. Organometallics 1998, 17, 999.
40. Cohen, R.; Milstein, D.; Martin, J. M. L. Organometallics 2004, 23, 2336.
41. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; 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, Revisions B.4, B.5, and C.1; Gaussian, Inc., Pittsburgh, PA, 2003.
42. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
43. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
44. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
45. Bergner, A.; Dolg, M.; Kuumlchle, W.; Stoll, H.; Preuszlig, H. Mol. Phys. 1993, 80, 1431.
46. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
47. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
48. Petersson, G. A.; Al-Laham, M. A. J. Chem. Phys. 1991, 94, 6081-6090.
49. Petersson, G. A.; Bennett, A.; Tensfeldt, T. G.; Al-Laham, M. A.; Shirley, W. A.; Mantzaris, J. J. Chem. Phys. 1988, 89, 2193-2218.
50. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.
51. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669-681.