Computational study on the mechanism and selectivity of C-H bond activation and dehydrogenative functionalization in the synthesis of rhazinilam

Journal of Organic Chemistry

Volumn 76, Issue 17, 2011, Pages 7180-7185

  Ellis, Corey S ^a   Ess, Daniel H ^a  

^a N243 Eyring Science Center   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

B3LYP DENSITY FUNCTIONAL; C-H ACTIVATION; C-H BOND; CARBOXYLATE GROUPS; CH-BOND ACTIVATION; COMPUTATIONAL STUDIES; CYCLOHEXYL; DIASTEREO-SELECTIVITY; ETHYL GROUPS; FUNCTIONALIZATIONS; HYDRIDE COMPLEXES; HYDRIDE ELIMINATION; PHENYL GROUP; REDUCTIVE ELIMINATION; TRANSITION STATE; WEAK INTERACTIONS;

ACTIVATION ANALYSIS; APPROXIMATION THEORY; CARBOXYLATION; HYDRIDES; METHANE; OLEFINS; PLATINUM;

PLATINUM COMPOUNDS;

ALKENE; CARBON; CARBOXYLIC ACID DERIVATIVE; HYDROGEN; METHANE; PHENYL GROUP; PLATINUM; RHAZINILAM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHIRALITY; COMPLEX FORMATION; DEHYDROGENATION; DIASTEREOISOMER; HYDROGEN BOND; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

ALKALOIDS; CARBON; COMPUTER SIMULATION; HYDROGEN; HYDROGEN BONDING; INDOLIZINES; LACTAMS; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS;

EID: 80052145300     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201234f     Document Type: Article

References (61)

1. Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731
2. Godula, K.; Sames, D. Science 2006, 312, 67
3. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
4. Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507
5. Bergman, R. G. Nature 2007, 446, 391
6. Hinman, A.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510
7. Das, S.; Incarvito, C. D.; Crabtree, R. H.; Brudvig, G. W. Science 2006, 312, 1941
8. Chen, M. S.; White, C. S. Science 2007, 318, 783
9. Newhouse, T.; Baren, P. S. Angew. Chem., Int. Ed. 2011, 50, 3362
10. Crabtree, R. H. Chem. Rev. 2010, 110, 575
11. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
12. Balcells, D.; Clot, E.; Eisenstein, O. Chem. Rev. 2010, 110, 749
13. Ryabov, A. D. Chem. Rev. 1990, 90, 403
14. Dyker, G. Angew. Chem., Int. Ed 1999, 38, 1690
15. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147 and references therein
16. For a recent example, see: Wang, D.-H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315
17. O'Malley, S. J.; Tran, K. L.; Watzke, A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2005, 127, 13496
18. Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 5767
19. Tasi, A. S.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 6316
20. Johnson, J. A.; Sames, D. J. Am. Chem. Soc. 2000, 122, 6321
21. Johnson, J. A.; Li, N.; Sames, D. J. Am. Chem. Soc. 2002, 124, 6900
22. Bowie, A. L.; Hughes, C. C.; Trauner, D. Org. Lett. 2005, 7, 5207
23. Bowie, A. L.; Traunder, D. J. Org. Chem. 2009, 74, 1581
24. Beck, E. M.; Hatley, R.; Gaunt, M. J. Angew. Chem., Int. Ed. 2008, 47, 3004
25. Ratcliffe, A. H.; Smith, G. F.; Smith, G. N. Tetrahedron Lett. 1973, 14, 5179
26. Magnus, P.; Rainey, T. Tetrahedron 2001, 57, 8647
27. Liu, Z.; Wasmuth, A. S.; Nelson, S. G. J. Am. Chem. Soc. 2006, 128, 10352
28. Gu, Z.; Zakarian, A. Org. Lett. 2010, 12, 4224
29. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
30. Wheeler, S. E.; Houk, K. N. J. Chem. Theory Comput. 2010, 6, 395
31. Frisch, M. J.; Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
32. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
33. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
34. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200
35. Frisch, M. J.; Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
36. CYLview, 1.0b; Legault, C. Y. Université de Sherbrooke, 2009, (http://www.cylview.org).
37. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157
38. Sieffert, N.; Bühl, M. Inorg. Chem. 2009, 48, 4622
39. Minenkov, Y.; Occhipinti, G.; Jensen, V. R. J. Phys. Chem. A 2009, 113, 11833
40. Stewart, I. C.; Benitez, D.; O'leary, D. J.; Tkatchouk, E.; Day, M. W.; Goddard, W. A., III; Grubbs, R. H. J. Am. Chem. Soc. 2009, 131, 1931
41. Benitez, D.; Tkatchouk, E.; Goddard, W. A., III. Organometallics 2009, 28, 2643
42. Fedorov, A.; Couzijn, E. P. A.; Nagornova, N. S.; Boyarkin, O. V.; Rizzo, T. R.; Chen, P. J. Am. Chem. Soc. 2010, 132, 13789
43. Takatani, T.; Sears, J. S.; Sherrill, C. D. J. Phys. Chem. A 2010, 114, 11714
44. Pratt, L. M.; Voit, S.; Okeke, F. N. J. Phys. Chem. A 2011, 115, 2281
45. Kulkarni, A. D.; Truhlar, D. G. J. Chem. Theory Comput. 2011, 7, 2325.
46. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270
47. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 284
48. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299
49. Ehlers, A. W.; Bohme, M.; Dapprich, S.; Gobbi, A.; Hollwarth, A.; Jonas, V.; Kohler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111
50. Roy, L. E.; Hay, P. J.; Martin, R. L. J. Chem. Theory Comput. 2008, 4, 1029
51. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378
52. Heiberg, H.; Swang, O.; Ryan, O. B.; Gropen, O. J. Phys. Chem. A 1999, 103, 10004
53. Heiberg, H.; Johansson, L.; Gropen, O.; Ryan, O. B.; Swang, O.; Tilset, M. J. Am. Chem. Soc. 2000, 122, 10831
54. Gilbert, T. M; Hristov, I.; Ziegler, T. Organometallics 2001, 20, 1183
55. Hristov, I. H.; Ziegler, T. Organometallics 2003, 22, 1668
56. Zhu, H.; Ziegler, T. Organometallics 2007, 26, 2277
57. Zhu, H.; Ziegler, T. Organometallics 2008, 27, 1743
58. Zhu, H.; Ziegler, T. Organometallics 2009, 28, 2773
59. Butschke, B.; Schröder, D.; Schwarz, H. Organometallics 2009, 28, 4340
60. For experimental work, see the work of Labinger and Bercaw. For example: Zhong, H. A.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2002, 124, 1378
61. For a review, see: Lin, Z. Coord. Chem. Rev. 2007, 251, 2280