Pd(II)-catalyzed intermolecular arylation of unactivated C(sp 3)-H bonds with aryl bromides enabled by 8-aminoquinoline auxiliary

Organic Letters

Volumn 16, Issue 8, 2014, Pages 2248-2251

  Wei, Yu ^a   Tang, Huarong ^a   Cong, Xuefeng ^a   Rao, Bin ^a   Wu, Chao ^a   Zeng, Xiaoming ^a  

^a XI'AN JIAOTONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84898940766     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500745t     Document Type: Article

References (57)

1. Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633
2. Transition Metal-Catalyzed Functionalization of Alkanes; Pérez, P. J., Ed.; Catalysis by Metal Complexes 38; Springer Science: Dordrecht, 2012.
3. Ackermann, L. Modern Arylation Methods; Wiley-VCH: Weinheim, 2009.
4. Yu, J.-Q.; Shi, Z.-J. Topics in Current Chemistry; Springer: Heidelberg, 2010; Vol. 292. For selected reviews on arylation, see
5. Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082
6. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
7. Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234
8. Godula, K.; Sames, D. Science 2006, 312, 67
9. Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
10. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
11. Wasa, M.; Engle, K. M.; Yu, J.-Q. Isr. J. Chem. 2010, 50, 605
12. Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem. Eur. J. 2010, 16, 2654
13. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
14. Li, H.; Li, B.-J.; Shi, Z.-J. Catal. Sci. Technol. 2011, 1, 191
15. Li, B.-J.; Shi, Z.-S. Chem. Soc. Rev. 2012, 41, 5588
16. Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902
17. Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726
18. He, J.; Wasa, M.; Chan, K. S. L.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 3387
19. Zhang, S.-Y.; Li, Q.; He, G.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2013, 135, 12135
20. Zhang, S.-Y.; He, G.; Nack, W. A.; Zhao, Y.; Li, Q.; Chen, G. J. Am. Chem. Soc. 2013, 135, 2124
21. He, G.; Zhao, Y.; Zhang, S.; Lu, C.; Chen, G. J. Am. Chem. Soc. 2012, 134, 3
22. Ano, Y.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 12984
23. Chen, F.-J.; Zhao, S.; Hu, F.; Chen, K.; Zhang, Q.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 4187
24. Chen, K.; Hu, F.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 3906
25. Shang, Y.; Jie, X.; Zhou, J.; Hu, P.; Huang, S.; Su, W. Angew. Chem., Int. Ed. 2013, 52, 1299
26. Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154
27. Shabashov, D.; Daugulis, O. Org. Lett. 2005, 7, 3657
28. Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965
29. Nadres, E. T.; Santos, G. I. F.; Shabashov, D.; Daugulis, O. J. Org. Chem. 2013, 78, 9689
30. Tran, L. D.; Daugulis, O. Angew. Chem., Int. Ed. 2012, 51, 5188
31. Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007, 129, 3510
32. Wang, D.-H.; Wasa, M.; Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 7190
33. Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 9886
34. Wasa, M.; Chan, K. S. L.; Zhang, X.-G.; He, J.; Miura, M.; Yu, J.-Q. J. Am. Chem. Soc. 2012, 134, 18570
35. Chan, K. S. L.; Wasa, M.; Chu, L.; Laforteza, B. N.; Miura, M.; Yu, J.-Q. Nat. Chem. 2014, 6, 146
36. He, G.; Chen, G. Angew. Chem., Int. Ed. 2011, 50, 5192
37. Nack, W. A.; He, G.; Zhang, S.-Y.; Lu, C.; Chen, G. Org. Lett. 2013, 15, 3440
38. Pan, F.; Shen, P.-X.; Zhang, L.-S.; Wang, X.; Shi, Z.-J. Org. Lett. 2013, 15, 4758
39. Zhang, Q.; Chen, K.; Rao, W.-H.; Zhang, Y.; Chen, F.-J.; Shi, B.-F. Angew. Chem., Int. Ed. 2013, 52, 13588
40. Reddy, B. V. S.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391
41. Gutekunst, W. R.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 19076
42. Shang, R.; Ilies, L.; Matsumoto, A.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 6030
43. Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2014, 136, 898
44. Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Angew. Chem., Int. Ed. 2011, 50, 7438
45. Lafrance, M.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570
46. Rousseaux, S.; Gorelsky, S. I.; Chung, B. K. W.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 10692
47. Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2008, 10, 1759
48. The example of Ni-catalyzed arylation using aryl bromides was recently disclosed. See: Li, M.; Dong, J.; Huang, X.; Li, K.; Wu, Q.; Song, F.; You, J. Chem. Commun. 2014, 50, 3944
49. Corbet, M.; De Campo, F. Angew. Chem., Int. Ed. 2013, 52, 9896
50. Asako, S.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 17755
51. Matsubara, T.; Asako, S.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2014, 136, 646
52. Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2013, 135, 5308
53. Aihara, Y.; Chatani, N. Chem. Sci. 2013, 4, 664
54. Wu, X.; Zhao, Y.; Ge, H. J. Am. Chem. Soc. 2014, 136, 1789
55. Tran, L. D.; Roane, J.; Daugulis, O. Angew. Chem., Int. Ed. 2013, 52, 6043
56. Song, M. S. W.; Lackner, M. S. S.; Ackermann, L. Angew. Chem., Int. Ed. 2014, 53, 2477
57. Zhang, C. A.; Erhardt, P. W. Synth. Commun. 2012, 42, 722 and references cited therein