Rhodium(III)-catalyzed azacycle-directed intermolecular insertion of arene C-H bonds into α-diazocarbonyl compounds

Journal of Organic Chemistry

Volumn 78, Issue 11, 2013, Pages 5444-5452

  Yu, Xinzhang ^a   Yu, Songjie ^a   Xiao, Jian ^a   Wan, Boshun ^a   Li, Xingwei ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; CATALYSIS;

C-C COUPLING; C-H BOND; CATALYTIC ALKYLATION; DIRECTING GROUPS; RHODIUM (III);

RHODIUM COMPOUNDS;

ALPHA DIAZOCARBONYL; CARBON; HYDROGEN; POLYCYCLIC AROMATIC HYDROCARBON; RHODIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; HYDROGEN BOND;

EID: 84879303041     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400572h     Document Type: Article

References (35)

1. Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169
2. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
3. Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013
4. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814
5. Song, G. Y.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
6. Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212
7. Wencel-Delord, J.; Dröge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740
8. Patureau, F. W.; Wencel-Delord, J.; Glorius, F. Aldrichimica Acta 2012, 45, 31
9. Boogaerts, I. I. F.; Nolan, S. P. J. Am. Chem. Soc. 2010, 132, 8858
10. Zeng, R.; Fu, C.; Ma, S. J. Am. Chem. Soc. 2012, 134, 9597
11. Wang, H.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 7318
12. Zhou, C.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 2302
13. Li, B.-J.; Shi, Z.-J. Chem. Sci. 2011, 2, 488
14. Tsai, A. S; Tauchert, M. E.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2011, 133, 1248
15. Li, Y.; Li, B.-J.; Wang, W.-H.; Huang, W.-P.; Zhang, X.-S.; Chen, K.; Shi, Z.-J. Angew. Chem., Int. Ed. 2011, 50, 2115
16. Hesp, K. D.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2012, 14, 2304
17. Li, Y.; Zhang, X.-S.; Chen, K.; He, K.-H.; Pan, F.; Li, B.-J.; Shi, Z.-J. Org. Lett. 2012, 14, 636
18. Yang, L.; Correia, C. A.; Li, C.-J. Adv. Synth. Catal. 2011, 353, 1269
19. Hesp, K. D.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2011, 133, 11430
20. Zhu, C.; Xie, W.; Falck, J. R. Chem.-Eur. J 2011, 17, 12591
21. Padwa, A.; Weingarten, M. D. J. Org. Chem. 2000, 65, 3722
22. Frampton, C. S.; Pole, D. L.; Yong, K.; Capretta, A. Tetrahedron Lett. 1997, 38, 5081
23. Miah, S.; Moody, C. J.; Richards, I. C.; Slawin, A. M. Z. J. Chem. Soc. Perkin Trans. 1 1997, 2405
24. Wee, A. G. H.; Lui, B.; Zhang, L. J. Org. Chem. 1992, 57, 4404
25. Padwa, A.; Austin, D. J.; Price, A. T.; Semones, M. A.; Doyle, M. P.; Protopopova, M. N.; Winchester, W. R.; Tran, A. J. Am. Chem. Soc. 1993, 115, 8669
26. Tsutsui, H.; Yamaguchi, Y.; Kitagaki, S.; Nakamura, S.; Anada, M.; Hashimoto, S. Tetrahedron: Asymmetry 2003, 14, 817
27. Hashimoto, S.; Watanabe, N.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1992, 1508
28. Candeias, N. R.; Gois, P. M. P.; Afonso, C. A. M. J. Org. Chem. 2006, 71, 5489
29. Pirrung, M. C.; Zhang, J.; Lackey, K.; Sternbach, D. D.; Brown, F. J. Org. Chem. 1995, 60, 2112
30. Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J.; Pflum, D. A.; Petsch, D. T. J. Am. Chem. Soc. 1997, 119, 9641
31. Zhao, X.; Wu, G.; Zhang, Y.; Wang J. Am. Chem. Soc. 2011, 133, 3296
32. Yao, T.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2012, 51, 775
33. Chan, W.-W.; Yeung, S.-H.; Zhou, Z.; Chan, A. S. C.; Yu, W.-Y. Org. Lett. 2010, 12, 604
34. Park, C. P.; Nagle, A.; Yoon, C. H.; Chen, C.; Jung, K. W. J. Org. Chem. 2009, 74, 6231
35. Chan, W.; Lo, S.-F.; Zhou, Z.; Yu, W.-Y. J. Am. Chem. Soc. 2012, 134, 13565