Reaction of N -isopropyl- N -phenyl-2,2′-bipyridin-6-amine with K2PtCl4: Selective C-H bond activation, C-N bond cleavage, and selective acylation

Organometallics

Volumn 32, Issue 17, 2013, Pages 4828-4836

  Carroll, Jeffrey ^a   Gagnier, Joshua P ^a   Garner, Alexander W ^a   Moots, Justin G ^a   Pike, Robert D ^b   Li, Yumin ^a   Huo, Shouquan ^a  

^a EAST CAROLINA UNIVERSITY   (United States)

^b William and Mary   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ANHYDRIDES; BOND DISSOCIATION; C-N BOND CLEAVAGES; CH-BOND ACTIVATION; CYCLOMETALATED COMPLEXES; ELECTRON DISTRIBUTIONS; INTRAMOLECULAR H-BONDING; X RAY CRYSTAL STRUCTURES;

ACETIC ACID; ACETONITRILE; ACTIVATION ANALYSIS; PH; REGIOSELECTIVITY;

ACYLATION;

EID: 84883754420     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om400540y     Document Type: Article

References (70)

1. Dunina, V. V.; Zalevskaya, O. A.; Potapov, V. M. Russ. Chem. Rev. 1988, 57, 434-473
2. Ryabov, A. D. Chem. Rev. 1990, 90, 403-424
3. Albrecht, M. Chem. Rev. 2010, 110, 576-623
4. Palladacycles: Synthesis, Characterization and Applications; Dupont, J.; Pfeffer, M., Eds.; Wiley-VCH: Weinheim, Germany, 2008.
5. Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507-514
6. Bergman, R. G. Nature 2007, 446, 391-393
7. Crosby, S. H.; Clarkson, G. J.; Rourke, J. P. J. Am. Chem. Soc. 2009, 131, 14142-14143
8. Thomas, H. R.; Deeth, R. J.; Clarkson, G. J.; Rourke, J. P. Organometallics 2011, 30, 5641-5648
9. Crosby, S. H.; Clarkson, G. J.; Rourke, J. P. Organometallics 2011, 30, 3603-3609
10. Crosby, S. H.; Deeth, R. J.; Clarkson, G. J.; Rourke, J. P. Dalton Trans. 2011, 40, 1227-1229
11. Campora, J.; Lopez, J. A.; Palma, P.; Valerga, P.; Spillner, E.; Carmona, E. H.; Peters, R. Angew. Chem., Int. Ed. 1999, 38, 147-151
12. Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527
13. Bedford, R. B. In Palladacycles: Synthesis, Characterization and Applications, Dupont, J.; Pfeffer, M., Eds, Wiley-VCH, Weinheim, 2008, pp 209-225.
14. Nájera, C.; Alonso, D. A. in Palladacycles: Synthesis, Characterization and Applications; Dupont, J.; Pfeffer, M., Eds.; Wiley-VCH: Weinheim, Germany; pp 155-207.
15. Kisala, J.; Ruman, T. Curr. Org. Chem. 2011, 15, 3486-3502
16. Dunina, V. V.; Gorunova, O. N.; Zykov, P. A.; Kochetkov, K. A. Russ. Chem. Rev. 2011, 80, 51-74
17. Goldman, A. S.; Roy, A. H.; Huang, Z.; Ahuja, R.; Schinski, W.; Brookhart, M. Science 2006, 312, 257-261
18. Huang, H.; Peters, R. Angew. Chem., Int. Ed. 2009, 48, 604-606
19. Williams, J. A. G.; Develay, S. D.; Rochester, D. L.; Murhy, L. Coord. Chem. Rev. 2008, 252, 2596-2611
20. Vezzu, D. A. K.; Deaton, J. C.; Jones, J. S.; Bartolotti, L.; Harris, C. F.; Marchetti, A. P.; Kondakova, M.; Pike, R. D.; Huo, S. Inorg. Chem. 2010, 49, 5107-5119
21. Deaton, J. C.; Young, R. H.; Lenhard, J. R.; Rajeswaran, M.; Huo, S. Inorg. Chem. 2010, 49, 9151-9161
22. Kalinowski, J.; Fattori, V.; Cocci, M.; Williams, J. A. G. Coord. Chem. Rev. 2011, 255, 2401-2425
23. Wang, Y.; Liu, Y.; Luo, J.; Qi, H.; Li, X.; Nin, M.; Liu, M.; Shi, D.; Zhu, W.; Cao, Y. Dalton Trans. 2011, 40, 5046-5051
24. Tamaru, Y.; Kagotani, M.; Yoshida, Z.-i. Angew. Chem., Int. Ed. 1981, 20, 980-981
25. Albert, J.; Ceder, R. M.; Gomez, M.; Granell, J.; Sales, J. Organometallics 1992, 11, 1536-1541
26. Alsters, P. L.; Engel, P. F.; Hogerheide, M. P.; Copijn, M.; Spek, A. L.; van Koten, G. Organometallics 1993, 12, 1831-1844
27. Cardenas, D. J.; Echavarren, A. M.; Vegas, A. Organometallics 1994, 13, 882-889
28. Dunina, V. V.; Golovan', E. B. Inorg. Chem. Commun. 1998, 1, 12-14
29. Zucca, A.; Cinellu, M. A.; Pinna, M. V.; Stoccoro, S.; Minghetti, G.; Manassero, M.; Sansoni, M. Organometallics 2000, 19, 4295-4303
30. Dunina, V. V.; Gorunova, O. N.; Averina, E. B.; Grishin, Y. K.; Kuz'mina, L. G.; Howard, J. A. K. J. Organomet. Chem. 2000, 603, 138-151
31. Stoccoro, S.; Soro, B.; Minghetti, G.; Zucca, A.; Cinellu, M. A. J. Organomet. Chem. 2003, 679, 1-9
32. Vazquez-Garcia, D.; Fernandez, A.; Lopez-Torres, M.; Rodriguez, A.; Gomez-Blanco, N.; Viader, C.; Vila, J. M.; Fernandez, J. J. Organometallics 2010, 29, 3303-3307
33. Minghetti, G.; Cinellu, M. A.; Chelucci, G.; Gladiali, S. J. Organomet. Chem. 1986, 307, 107-114
34. Sana, G.; Minghetti, G.; Zucca, A.; Pilo, L. I.; Seeber, R.; Laschi, F. Inorg. Chim. Acta 2000, 305, 189-205
35. Minghetti, G.; Cinellu, M. A.; Stoccoro, S.; Zucca, A.; Manassero, M. J. Chem. Soc., Dalton Trans. 1995, 777-781
36. Wong-Foy, A. G.; Henling, L. M.; Day, M.; Labinger, J. A.; Bercaw, J. E. J. Mol. Catal. A: Chem. 2002, 189, 3-16
37. Garner, A. W.; Harris, C. F.; Vezzu, D. A. K.; Pike, R. D.; Huo, S. Chem. Commun. 2011, 47, 1902-1904
38. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry: Part A: Structure and Mechanism, 5 th ed.; Springer: New York, 2007; p 258.
39. Yang, J.-S.; Lin, Y.-H.; Yang, C.-S. Org. Lett. 2002, 4, 777-780
40. Vezzu, D. A. K.; Ravindranathan, D.; Garner, A. W.; Bartolotti, L.; Smith, M. E.; Boyle, P. D.; Huo, S. Inorg. Chem. 2011, 50, 8261-8273
41. Huo, S.; Harris, C. F.; Vezzu, D. A. K.; Gagnier, J.; Smith, M. E.; Pike, R.; Li, Y. Polyhedron 2013, 52, 1030-1040
42. Lu, W.; Mi, B.-X.; Chan, M. C. W.; Hui, Z.; Che, C.-M.; Zhu, N.; Lee, S. T. J. Am. Chem. Soc. 2004, 126, 4958-4971
43. Ravindranathan, D.; Vezzu, D. A. K.; Bartolotti, L.; Boyle, P. D.; Huo, S. Inorg. Chem. 2010, 49, 8922-8928
44. Dunina, V. V.; Gorunova, O. N. Russ. Chem. Rev. 2005, 74, 871-913
45. Sajith, P. K.; Suresh, C. H. Dalton Trans. 2010, 39, 815-822
46. Hickinbottom, W. J. J. Chem. Soc. 1933, 1070-1073
47. Guibe, F. Tetrahedron 1998, 54, 2967-3320
48. Gandelman, M.; Milstein, D. Chem. Commun. 2000, 1603-1604
49. Lin, B. L.; Clough, C. R.; Hillhouse, G. L. J. Am. Chem. Soc. 2002, 124, 2890-2891
50. Ozerov, O. V.; Guo, C.; Papkov, V. A.; Foxman, B. M. J. Am. Chem. Soc. 2004, 126, 4792-4793
51. Weng, W.; Guo, C.; Moura, C.; Yang, L.; Foxman, B. W.; Ozerov, O. V. Organometallics 2005, 24, 3487-3499 and references cited therein
52. Collman, J. P.; Wang, H. J. H.; Decreau, R. A.; Eberspacher, T. A.; Sunderland, C. J. Chem. Commun. 2005, 2497-2499
53. Ryabov, A. D. Inorg. Chem. 1987, 26, 1252-1260
54. Ryabov, A. D.; van Eldik, R. Angew. Chem., Int. Ed. 1994, 33, 783-784
55. Aoki, S.; Matsuo, Y.; Ogura, S.; Ohwada, H.; Hisamatsu, Y.; Moromizato, S.; Shiro, M.; Kitamura, M. Inorg. Chem. 2011, 50, 806-818
56. Arm, K. J.; Williams, J. A. G. Chem. Commun. 2005, 230-232
57. Holton, R. A.; Natalie, K. J., Jr. Tetrahedron Lett. 1981, 22, 267-270
58. Clark, P. W.; Dyke, H. J.; Dyke, S. F.; Perry, G. J. Organomet. Chem. 1983, 253, 399-413
59. Lundgren, R. J.; Sappong-Kumankumah, A.; Stradiotto, M. Chem. Eur. J 2010, 16, 1983-1991
60. Fang, Y.-Q.; Hanan, G. S. Synlett 2003, 852-854
61. SAINT PLUS; Bruker Analytical X-ray Systems, Madison, WI, 2001.
62. SADABS: Bruker Analytical X-ray Systems, Madison, WI, 2001.
63. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122
64. Gaussian 03, Revision C.02; Gaussian, Inc., Wallingford, CT, 2004.
65. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
66. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
67. Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297-3305
68. Dunning, T. H. J. Chem. Phys. 1989, 90, 1007-1023
69. Scuseria, G. E.; Janssen, C. L.; Schaefer, H. F., III J. Chem. Phys. 1988, 89, 7382-7387
70. Scuseria, G. E.; Schaefer, H. F., III J. Chem. Phys. 1989, 90, 3700-3703