Understanding reactivity and stereoselectivity in palladium-catalyzed diastereoselective sp 3 C-H Bond activation: Intermediate characterization and computational studies

Journal of the American Chemical Society

Volumn 134, Issue 34, 2012, Pages 14118-14126

  Giri, Ramesh ^a   Lan, Yu ^b   Liu, Peng ^b   Houk, K N ^b   Yu, Jin Quan ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOXYLATION; C-H ACTIVATION; C-H BOND; C-H BOND CLEAVAGE; C-H INSERTION; CH-BOND ACTIVATION; COMPUTATIONAL INVESTIGATION; COMPUTATIONAL STUDIES; DENSITY FUNCTIONAL THEORIES (DFT); DFT CALCULATION; DIASTEREO-SELECTIVITY; DIASTEREOMERS; DIASTEREOSELECTIVE; DIASTEREOSELECTIVITIES; OXAZOLINES; PALLADIUM-CATALYZED; STERIC REPULSIONS; STRUCTURAL INFORMATION; THEORETICAL PREDICTION; THROUGH THE LENS; TRANSITION STATE;

ACTIVATION ANALYSIS; CATALYSIS; CHEMICAL BONDS; DENSITY FUNCTIONAL THEORY; NITROGEN COMPOUNDS; ORGANIC POLYMERS; PALLADIUM COMPOUNDS; STEREOCHEMISTRY;

STEREOSELECTIVITY;

CARBON; HYDROGEN; OXAZOLINE DERIVATIVE; PALLADIUM;

ACETOXYLATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; CRYSTAL STRUCTURE; CRYSTALLIZATION; DENSITY FUNCTIONAL THEORY; IODINATION; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 84865632722     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja304643e     Document Type: Article

References (64)

1. Hartwig, J. F. Nature 2008, 455, 314
2. Hartwig, J. F.; Cook, K. S.; Hapke, M.; Incarvito, C. D.; Fan, Y. B.; Webster, C. E.; Hall, M. B. J. Am. Chem. Soc. 2005, 127, 2538
3. Du Bois, J. Chemtracts 2005, 18, 1
4. Periana, R. A.; Bhalla, G.; Tenn, W. J.; Young, K. J. H.; Liu, X. Y.; Mironov, O.; Jones, C. J.; Ziatdinov, V. R. J. Mol. Catal. A 2004, 220, 7
5. Crabtree, R. H. J. Organomet. Chem. 2004, 689, 4083
6. Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2180
7. Sen, A. Acc. Chem. Res. 1998, 31, 550
8. Shilov, A. E.; Shulpin, G. B. Chem. Rev. 1997, 97, 2879
9. Ryabov, A. D. Chem. Rev. 1990, 90, 403
10. Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861
11. Yu, J. Q.; Giri, R.; Chen, X. Org. Biomol. Chem. 2006, 4, 4041
12. Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q. N.; Lazareva, A. Synlett 2006, 3382
13. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
14. Garcia-Cuadrado, D.; de Mendoza, P.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2007, 129, 6880
15. Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066
16. Davies, D. L.; Donald, S. M. A.; Macgregor, S. A. J. Am. Chem. Soc. 2005, 127, 13754
17. Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 10848
18. Lafrance, M.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570
19. Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754
20. Rousseaux, S.; Gorelsky, S. I.; Chung, B. K. W.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 10692
21. Balcells, D.; Clot, E.; Eisenstein, O. Chem. Rev. 2010, 110, 749
22. Ke, Z.; Cundari, T. R. Organometallics 2010, 29, 821
23. Musaev, D. G.; Kaledin, A.; Shi, B. F.; Yu, J. Q. J. Am. Chem. Soc. 2012, 134, 1690
24. Gomez, M.; Granell, J.; Martinez, M. J. Chem. Soc., Dalton Trans. 1998, 37
25. Ryabov, A. D.; Sakodinskaya, I. K.; Yatsimirsky, A. K. J. Chem. Soc., Dalton Trans. 1985, 2629
26. Giri, R.; Liang, J.; Lei, J. G.; Li, J. J.; Wang, D. H.; Chen, X.; Naggar, I. C.; Guo, C. Y.; Foxman, B. M.; Yu, J. Q. Angew. Chem., Int. Ed. 2005, 44, 7420
27. Giri, R.; Chen, X.; Yu, J. Q. Angew. Chem., Int. Ed. 2005, 44, 2112
28. Dick, A. R.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 12790
29. Powers, D. C.; Ritter, T. Nat. Chem. 2009, 1, 302
30. Powers, D. C.; Geibel, M. A. L.; Klein, J. E. M. N.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 17050
31. Khusnutdinova, J. R.; Rath, N. P.; Mirica, L. M. J. Am. Chem. Soc. 2010, 132, 7303
32. Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242
33. Whitesides, T. H.; Arhart, R. W. Tetrahedron Lett. 1972, 13, 297
34. Schroder, D.; Schwarz, H. J. Am. Chem. Soc. 1993, 115, 8818
35. Schroder, D.; Zummack, W.; Schwarz, H. J. Am. Chem. Soc. 1994, 116, 5857
36. Loos, J.; Schroder, D.; Zummack, W.; Schwarz, H. Int. J. Mass Spectrom. 2002, 217, 169
37. Hornung, G.; Schroder, D.; Schwarz, H. J. Am. Chem. Soc. 1997, 119, 2273
38. Ma, Y. O.; Bergman, R. G. Organometallics 1994, 13, 2548
39. Mobley, T. A.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 3253
40. Keyes, M. C.; Young, V. G.; Tolman, W. B. Organometallics 1996, 15, 4133
41. Johnson, J. A.; Ning, L.; Sames, D. J. Am. Chem. Soc. 2002, 124, 6900
42. Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567
43. Covell, D. J.; White, M. C. Angew. Chem., Int. Ed. 2008, 47, 6448
44. Groves, J. T.; Viski, P. J. Am. Chem. Soc. 1989, 111, 8537
45. Larrow, J. F.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 12129
46. Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192
47. Harada, H.; Thalji, R. K.; Bergman, R. G.; Ellman, J. A. J. Org. Chem. 2008, 73, 6772
48. Zalatan, D. N.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 9220
49. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Yu, W. Y.; Che, C. M. Angew. Chem., Int. Ed. 2002, 41, 3465
50. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127
51. Meyers, A. I. Acc. Chem. Res. 1978, 11, 375
52. Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984
53. Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496
54. Meyers, A. I. J. Org. Chem. 2005, 70, 6137
55. Hargaden, G. C.; Guiry, P. J. Chem. Rev. 2009, 109, 2505
56. Balavoine, G.; Clinet, J. C.; Zerbib, P.; Boubekeur, K. J. Organomet. Chem. 1990, 389, 259
57. Balavoine, G.; Clinet, J. C. J. Organomet. Chem. 1990, 390, C84
58. A part of the current research work has been published elsewhere: Giri, R., Ph.D. Thesis, The Scripps Research Institute, 2009.
59. Moyano, A.; Rosol, M.; Moreno, R. M.; Lopez, C.; Maestro, M. A. Angew. Chem., Int. Ed. 2005, 44, 1865
60. Giri, R.; Chen, X.; Hao, X. S.; Li, J. J.; Liang, J.; Fan, Z. P.; Yu, J. Q. Tetrahedron-Asymmetry 2005, 16, 3502
61. Gomez, M.; Granell, J.; Martinez, M. Organometallics 1997, 16, 2539
62. Stephens, T. A.; Morehous, S. M.; Powell, A. R.; Heffer, J. P.; Wilkinson, G. J. Chem. Soc. 1965, 3632
63. Bakhmutov, V. I.; Berry, J. F.; Cotton, F. A.; Ibragimov, S.; Murillo, C. A. Dalton Trans. 2005, 1989
64. Frisch, M. J.; Gaussian 09, Rev. B.01; Gaussian, Inc., Wallingford, CT, 2010.