Synthesis and reactivity of an iridium(I) acetonyl PNP complex. Experimental and computational study of metal-ligand cooperation in H-H and C-H bond activation via reversible ligand dearomatization

Organometallics

Volumn 29, Issue 17, 2010, Pages 3817-3827

  Schwartsburd, Leonid ^a   Iron, Mark A ^a   Konstantinovski, Leonid ^a   Diskin Posner, Yael ^a   Leitus, Gregory ^a   Shimon, Linda J W ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

APICAL POSITIONS; BENZYLIC; C-H ACTIVATION; C-H BOND; CH-BOND ACTIVATION; COMPUTATIONAL STUDIES; CYCLOOCTENE; DEAROMATIZATION; DFT STUDY; DIHYDRIDES; ELECTRON-RICH; PROTON MIGRATION;

ACETONE; ACTIVATION ANALYSIS; BENZENE; DEUTERIUM COMPOUNDS; IRIDIUM; LIGANDS; PROTONS; SYNTHESIS (CHEMICAL);

IRIDIUM COMPOUNDS;

EID: 77956405900     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1004435     Document Type: Article

References (73)

1. Grutzmacher, H. Angew. Chem., Int. Ed. 2008, 47, 1814 and references therein.
2. Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40
3. Clapham, S. E.; Hadzovic, A.; Morris, R. H. Coord. Chem. Rev. 2004, 248, 2201
4. Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300
5. Maire, P.; Buttner, T.; Breher, F.; Le Floch, P.; Grutzmacher, H. Angew. Chem., Int. Ed. 2005, 44, 6318
6. Fryzuk, M. D.; MacNeil, P. A. Organometallics 1983, 2, 682
7. Samec, J. S. M.; Backvall, J. E.; Andersson, P. G.; Brandt, P. Chem. Soc. Rev. 2006, 35, 237
8. Casey, C. P.; Beetner, S. E.; Johnson, J. B. J. Am. Chem. Soc. 2008, 130, 2285
9. Shvo, Y.; Czarkie, D.; Rachamim, Y. J. Am. Chem. Soc. 1986, 108, 7400
10. Bullock, R. M. Chem. Eur. J. 2004, 10, 2366
11. For PCP and PCN systems see: Ashkenazi, N.; Vigalok, A.; Parthiban, S.; Ben-David, Y.; Shimon, L. J. W.; Martin, J. M. L.; Milstein, D. J. Am. Chem. Soc. 2000, 122, 8797
12. Frech, C. M.; Ben-David, Y.; Weiner, L.; Milstein, D. J. Am. Chem. Soc. 2006, 128, 7128
13. Poverenov, E.; Gandelman, M.; Shimon, L. J. W.; Rozenberg, H.; Ben-David, Y.; Milstein, D. Organometallics 2005, 24, 1082
14. For a review on PNP systems and their analogues see: van der Vlugt, J. I.; Reek, J. N. H. Angew. Chem., Int. Ed. 2009, 48, 8832 Cooperativity in an aliphatic PNP-Ru complex
15. Friedrich, A.; Drees, M.; Gunne, J. S.; Schneider, S. J. Am. Chem. Soc. 2009, 131, 17552
16. Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 2005, 127, 10840
17. Zhang, J.; Shimon, L. J. W.; Milstein, D. Dalton Trans. 2006, 107
18. Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2006, 45, 1113
19. Gunanathan, C.; Ben-David, Y.; Milstein, D. Science 2007, 317, 790
20. Gunanathan, C.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2009, 131, 3146
21. Gunanathan, C.; Milstein, D. Angew. Chem., Int. Ed. 2008, 47, 8661
22. Gnanaprakasam, B.; Zhang, J.; Milstein, D. Angew. Chem., Int. Ed. 2010, 49, 1468
23. Kohl, S. W.; Weiner, L.; Schwartsburd, L.; Konstantinovski, L.; Shimon, L. J. W.; Ben-David, Y.; Iron, M. A.; Milstein, D. Science 2009, 324, 74
24. Ben Ari, E.; Leitus, G.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2006, 128, 15390
25. Iron, M. A.; Ben-Ari, E.; Cohen, R.; Milstein, D. Dalton Trans. 2009, 9433
26. Zeng, G.; Guo, Y.; Li, S. Inorg. Chem. 2009, 48, 10257
27. For acetonyl complexes of iridium see: Feller, M.; Karton, A.; Leitus, G.; Martin, J. M. L.; Milstein, D. J. Am. Chem. Soc. 2006, 128, 12400
28. Arndtsen, B. A.; Bergman, R. G. J. Organomet. Chem. 1995, 504, 143
29. Milstein, D. Acc. Chem. Res. 1984, 17, 221
30. Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773 For acetonyl complexes of rhodium see
31. de Pater, B. C.; Fruhauf, H. W.; Goubitz, K.; Fraanje, J.; Budzelaar, P. H. M.; Gal, A. W.; Vrieze, K. Inorg. Chim. Acta 2005, 358, 431
32. Milstein, D. J. Am. Chem. Soc. 1982, 104, 5227 For acetonyl complexes of palladium see
33. Vicente, J.; Arcas, A.; Fernandez-Hernandez, J. M.; Bautista, D. Organometallics 2001, 20, 2767
34. Vicente, J.; Arcas, A.; Fernandez-Hernandez, J. M.; Bautista, D. Organometallics 2008, 27, 3978 For acetonyl complexes of platinum see:
35. Falvello, L. R.; Garde, R.; Miqueleiz, E. M.; Tomas, M.; Urriolabeitia, E. P. Inorg. Chim. Acta 1997, 264, 297
36. Vicente, J.; Arcas, A.; Fernndez-Hernndez, J. M.; Aulln, G.; Bautista, D. Organometallics 2007, 26, 6155
37. 4 resulted in a mixture of products.
38. 2 with the PNP ligand, was described: Hermann, D.; Gandelman, M.; Rozenberg, H.; Shimon, L. J. W.; Milstein, D. Organometallics 2002, 21, 812
39. Kloek, S. M.; Heinekey, D. M.; Goldberg, K. I. Organometallics 2006, 25, 3007
40. Findlater, M.; Bernskoetter, W. H.; Brookhart, M. J. Am. Chem. Soc. 2010, 132, 4534
41. Li, S. H.; Hall, M. B. Organometallics 1999, 18, 5682
42. Rybtchinski, B.; Ben-David, Y.; Milstein, D. Organometallics 1997, 16, 3786
43. Laporte, C.; Buttner, T.; Ruegger, H.; Geier, J.; Schonberg, H.; Grutzmacher, H. Inorg. Chim. Acta 2004, 357, 1931
44. Dahlenburg, L.; Gotz, R. Inorg. Chim. Acta 2004, 357, 2875
45. Nemeh, S.; Flesher, R. J.; Gierling, K.; Maichle-Moessmer, C.; Mayer, H. A.; Kaska, W. C. Organometallics 1998, 17, 2003
46. Brown, J. M.; Dayrit, F. M.; Lightowler, D. J. Chem. Soc., Chem. Commun. 1983, 8, 414
47. Since H/D scrambling at the benzylic positions might take place upon prolonged heating in the presence of the acetone generated in the reaction, the reaction solution was heated for the minimal period required for full conversion.
48. Since trace amounts of adventitious water are sufficient for proton transfer catalysis, experiments in the complete absence of water were not practical. Experiments aimed at exploring the rate effect of controlled concentrations of water in a water-miscible solvent are planned.
49. 5)H is inhibited by the coordination of CO. See: Rosini, G. P.; Wang, K.; Patel, B.; Goldman, A. S. Inorg. Chim. Acta 1998, 270, 537
50. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.;; Fox, D. J. Gaussian 09, Revision A.02; Gaussian, Inc., Wallingford, CT, 2009.
51. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157
52. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
53. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 194101
54. Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry 3: Methods of Electronic Structure Theory; Schaefer, H. F., III, Ed.; Plenum Press: New York, 1977; Vol. 3, pp 1 - 28.
55. Dolg, M. In Modern Methods and Algorithms of Quantum Chemistry; Grotendorst, J., Ed.; John von Neumann Institute for Computing: Jülich, Germany, 2000; Vol. 3, pp 507 - 540.
56. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007
57. Martin, J. M. L.; Sundermann, A. J. Chem. Phys. 2001, 114, 3408
58. Dunlap, B. I. J. Chem. Phys. 1983, 78, 3140-3142
59. Dunlap, B. I. J. Mol. Struct. (THEOCHEM) 2000, 529, 37
60. Schwabe, T.; Grimme, S. Phys. Chem. Chem. Phys. 2007, 9, 3397
61. Schwabe, T.; Grimme, S. Acc. Chem. Res. 2008, 41, 569
62. Grimme, S. J. Comput. Chem. 2006, 27, 1787
63. Karton, A.; Tarnopolsky, A.; Lamère, J.-F.; Schatz, G. C.; Martin, J. M. L. J. Phys. Chem. A 2008, 112, 12868
64. Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, 5151
65. Cancès, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032
66. Cossi, M.; Barone, V.; Mennucci, B.; Tomasi, J. Chem. Phys. Lett. 1998, 286, 253
67. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43
68. Mennucci, B.; Cancès, E.; Tomasi, J. J. Phys. Chem. B 1997, 101, 10506
69. Tomasi, J.; Mennucci, B.; Cancès, E. J. Mol. Struct. (THEOCHEM) 1999, 464, 211
70. Wheeler, S. E.; Houk, K. N. J. Chem. Theory Comput. 2010, 6, 395
71. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523
72. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154
73. Fukui, K. Acc. Chem. Res. 1981, 14, 363