Mechanistic insight into asymmetric N-H insertion cooperatively catalyzed by a dirhodium compound and a spiro chiral phosphoric acid

Organometallics

Volumn 33, Issue 15, 2014, Pages 4042-4050

  Wang, Xu Chao ^a,b   Song, Xian Shuang ^a   Guo, Li Ping ^a   Qu, Deyu ^a   Xie, Zhi Zhong ^a   Verpoort, Francis ^a   Cao, Jun ^c  

^a School of Materials Science and Engineering   (China)

^b WUHAN UNIVERSITY OF TECHNOLOGY   (China)

^c BEIJING NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; ORGANIC COMPOUNDS; PHOSPHORIC ACID;

ACTIVATION FREE ENERGY; CARBENOIDS; CATALYTIC CYCLES; DENSITY FUNCTIONAL THEORY METHODS; DIAZOACETATE; ENAMINE INTERMEDIATES; N-H INSERTION; TWO-STEP PROCESS;

REACTION INTERMEDIATES;

EID: 84905864474     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om5005572     Document Type: Article

References (39)

1. Buck, R. T.; Clarke, P. A.; Coe, D. M.; Drysdale, M. J.; Ferris, L.; Haigh, D.; Moody, C. J.; Pearson, N. D.; Swann, E. Chem. Eur. J. 2000, 6, 2160-2167
2. Clapham, B.; Spanka, C.; Janda, K. D. Org. Lett. 2001, 3, 2173-2176
3. Qian, Y.; Jing, C. C.; Liu, S. Y.; Hu, W. H. Chem. Commun. 2013, 49, 2700-2702
4. Guo, X.; Hu, W. H. Acc. Chem. Res. 2013, 46, 2427-2440
5. Xu, B.; Zhu, S. F.; Xie, X. L.; Shen, J. J.; Zhou, Q. L. Angew. Chem., Int. Ed. 2011, 50, 11483-11486
6. Goto, T.; Takeda, K.; Shimada, N.; Nambu, H.; Anada, M.; Shiro, M.; Ando, K.; Hashimoto, S. Angew. Chem., Int. Ed. 2011, 50, 6803-6808
7. Saito, H.; Uchiyama, T.; Miyake, M.; Anada, M.; Hashimoto, S.; Takabatake, T.; Miyairi, S. Heterocycles 2010, 81, 1149-1155
8. Xie, J.-H.; Zhou, Q.-L. Acc. Chem. Res. 2008, 41, 581-593
9. Mieusset, J. L.; Bespokoev, A.; Pacar, M.; Abraham, M.; Arion, V. B.; Brinker, U. H. J. Org. Chem. 2008, 73, 6551-6558
10. Moody, C. J. Angew. Chem., Int. Ed. 2007, 46, 9148-9150
11. Ferris, L.; Haigh, D.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 1996, 2885-2888
12. Garcia, C. F.; McKervey, M. A.; Ye, T. Chem. Commun. 1996, 1465-1466
13. Buck, R. T.; Moody, C. J.; Pepper, A. G. Arkivoc 2002, 16-32
14. Ferris, L.; Haigh, D.; Moody, C. J. Tetrahedron Lett. 1996, 37, 107-110
15. Saito, H.; Morita, D.; Uchiyama, T.; Miyake, M.; Miyairi, S. Tetrahedron Lett. 2012, 53, 6662-6664
16. Lee, E. C.; Fu, G. C. J. Am. Chem. Soc. 2007, 129, 12066-12067
17. Liu, B.; Zhu, S.-F.; Zhang, W.; Chen, C.; Zhou, Q.-L. J. Am. Chem. Soc. 2007, 129, 5834-5835
18. Zhu, S. F.; Zhou, Q. L. Acc. Chem. Res. 2012, 45, 1365-1377
19. Zhu, S. F.; Xu, B.; Wang, G. P.; Zhou, Q. L. J. Am. Chem. Soc. 2012, 134, 436-442
20. Gillingham, D.; Fei, N. Chem. Soc. Rev. 2013, 42, 4918-4931
21. Xie, Z.-Z.; Liao, W.-J.; Cao, J.; Guo, L.-P.; Verpoort, F.; Fang, W. Organometallics 2014, 33, 2448-2456
22. Li, Z.; Parr, B. T.; Davies, H. M. L. J. Am. Chem. Soc. 2012, 134, 10942-10946
23. Liang, Y.; Zhou, H.; Yu, Z.-X. J. Am. Chem. Soc. 2009, 131, 17783-17785
24. Xu, B.; Zhu, S.-F.; Zhang, Z.-C.; Yu, Z.-X.; Ma, Y.; Zhou, Q.-L. Chem. Sci. 2014, 5, 1442-1448
25. Frisch, M. J., GAUSSIAN 09, Revision A.1; Gaussian, Inc., Wallingford, CT, 2009.
26. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B: Condens. Matter 1988, 37, 785-789
27. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
28. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1977, 66, 4377-4384
29. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310
30. Fukui, K. Acc. Chem. Res. 1981, 14, 363-368
31. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396
32. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 194101(1-18)
33. Benitez, D.; Tkatchouk, E.; Goddard, W. A. Organometallics 2009, 28, 2643-2645
34. Xu, X. F.; Liu, P.; Shu, X. Z.; Tang, W. P.; Houk, K. N. J. Am. Chem. Soc. 2013, 135, 9271-9274
35. Nakamura, E.; Yoshikai, N.; Yamanaka, M. J. Am. Chem. Soc. 2002, 124, 7181-7192
36. Xue, J.; Luk, H. L.; Platz, M. S. J. Am. Chem. Soc. 2011, 133, 1763-1765
37. Jiang, J.; Xu, H. D.; Xi, J. B.; Ren, B. Y.; Lv, F. P.; Guo, X.; Jiang, L. Q.; Zhang, Z. Y.; Hu, W. H. J. Am. Chem. Soc. 2011, 133, 8428-8431
38. Shi, F. Q.; Li, X.; Xia, Y.; Zhang, L.; Yu, Z. X. J. Am. Chem. Soc. 2007, 129, 15503-15512
39. Hirata, T.; Yamanaka, M. Chem. Asian J. 2011, 6, 510-516