C-CN vs C-H cleavage of benzonitrile using [(dippe)PtH]2

Organometallics

Volumn 30, Issue 6, 2011, Pages 1523-1529

  Swartz, Brett D ^a   Brennessel, William W ^a   Jones, William D ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZONITRILES; C-H ACTIVATION; REGIOISOMERS; TWO-PRODUCT;

ACTIVATION ANALYSIS; BENZENE;

PLATINUM;

EID: 79952968792     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om101069j     Document Type: Article

References (39)

1. For reviews of C-C activation by organometallic complexes: Murakami, M.; Ito, Y. In Topics in Organometallic Chemistry; Murai, S., Ed.; Springer-Verlag: New York, 1999; p 97.
2. Rybtchinski, B.; Milstein, M. Angew. Chem., Int. Ed. 1999, 38, 870
3. Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Simhai, N.; Iverson, C. N.; Müller, C.; Satoh, T.; Jones, W. D. J. Mol. Catal. A 2002, 189, 157
4. Matsuda, T.; Shigeno, M.; Murakami, M. Org. Lett. 2008, 10, 5219
5. Ashida, S.; Murakami, M. Bull. Chem. Soc. Jpn. 2008, 81, 885
6. Matsuda, T.; Tsuboi, T.; Murakami, M. J. Am. Chem. Soc. 2007, 129, 2596
7. Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540
8. Wentzel, M. T.; Reddy, V. J.; Hyster, T. K.; Douglas, C. J. Angew. Chem., Int. Ed. 2009, 48, 6121
9. Dreis, A. M.; Douglas, C. J. J. Am. Chem. Soc. 2009, 131, 412
10. Garcia, J. J.; Jones, W. D. Organometallics 2000, 19, 5544
11. Garcia, J. J.; Brunkan, N. M.; Jones, W. D. J. Am. Chem. Soc. 2002, 124, 9547
12. Garcia, J. J.; Arévalo, A.; Brunkan, N. M.; Jones, W. D. Organometallics 2004, 23, 3997
13. Taw, F. L.; White, P. S.; Bergman, R. G.; Brookhart, M. J. Am. Chem. Soc. 2002, 124, 4192
14. Taw, F. L.; Mueller, A. H.; Bergman, R. G.; Brookhart, M. J. Am. Chem. Soc. 2003, 125, 9808
15. Nakao, Y. N.; Hirata, Y.; Tanaka, M.; Hiyama, T. Angew. Chem., Int. Ed. 2008, 47, 385
16. Nakao, Y.; Yukawa, T.; Hirata, Y.; Oda, S.; Satoh, J.; Hiyama, T. J. Am. Chem. Soc. 2006, 128, 7116
17. Nakao, Y.; Ebata, S.; Yada, A.; Hiyama, T.; Ikawa, M.; Ogoshi, S. J. Am. Chem. Soc. 2008, 130, 12874
18. Watson, M. P.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 12594
19. van der Vlugt, J. I.; van Duren, R.; Batema, G; den Heeten, R.; Meetsma, A.; Fraanje, J.; Goubitz, K.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Vogt, D. Organometallics 2005, 24, 5377
20. Tobisu, M.; Nakamura, R.; Kita, Y.; Chatani, N. Bull. Korean Chem. Soc. 2010, 31, 582
21. Kita, Y.; Tobisu, M.; Chatani, N. Org. Lett. 2010, 12, 1864
22. Tobisu, M.; Nakamura, R.; Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 3174
23. Tobisu, M.; Kita, Y.; Ano, Y.; Chatani, N. J. Am. Chem. Soc. 2008, 130, 15982
24. Tobisu, M.; Chatani, N. Chem. Soc. Rev. 2008, 37, 300
25. Miller, J. A. Tetrahedron Lett. 2001, 42, 6991
26. Miller, J. A.; Dankwardt, J. W. Tetrahedron Lett. 2003, 44, 1907
27. Miller, J. A.; Dankwardt, J. W.; Penney, J. M. Synthesis 2003, 1643
28. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. In Principles and Applications of Organtransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
29. Tolman, C. A.; McKinney, R. J.; Seidel, W. C.; Druliner, J. D.; Stevens, W. R. Adv. Catal. 1985, 33, 1
30. Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. Organometallics 1999, 18, 4040
31. Simhai, N.; Iverson, C. N.; Edelbach, B. L.; Jones, W. D. Organometallics 2001, 20, 2759 See also ref 11b. Iverson, C. N.; Lachicotte, R. J.; Müller, C.; Jones, W. D. Organometallics 2002, 21, 5320
32. Hackett, M.; Ibers, J. A.; Whitesides, G. M. J. Am. Chem. Soc. 1988, 110, 1436
33. Hackett, M.; Whitesides, G. M. J. Am. Chem. Soc. 1988, 110, 1449
34. Edelbach, B. L.; Vicic, D. A.; Lachicotte, R. J.; Jones, W. D. Organometallics 1998, 17, 4784
35. Edelbach, B. L.; Vicic, D. A.; Lachicotte, R. J.; Jones, W. D. J. Am. Chem. Soc. 1998, 120, 2843
36. 2 refer to: Schwartz, D. J.; Andersen, R. A. J. Am. Chem. Soc. 1995, 117, 4014
37. 2.
38. Carey, F. A.; Sundberg, R. J. In Advanced Organic Chemistry Part A: Structure and Mechanisms; Springer: Charlottesville, VA, 2000.
39. Krasovskiy, A.; Knochel, P. Pract. Synth. Proc. 2006, 5, 890