Pd(II)-Catalyzed Pyridine N -Oxides Directed Arylation of Unactivated Csp3-H Bonds

Journal of Organic Chemistry

Volumn 80, Issue 9, 2015, Pages 4618-4626

  Liu, Jianzhong ^a   Xie, Ying ^b   Zeng, Wei ^b   Lin, Dongen ^b   Deng, Yuanfu ^b   Lu, Xiaoxia ^a  

^a CHENGDU INSTITUTE OF BIOLOGY   (China)

^b SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; CATALYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PYRIDINE;

ALIPHATIC AMIDES; ALKYL CARBOXYLIC ACIDS; ARYL GROUP; ARYL IODIDES; ARYLATIONS; CHEMICAL EQUATIONS; PYRIDINE N-OXIDE;

PALLADIUM COMPOUNDS;

AMIDE; IODIDE; PALLADIUM; PYRIDINE 1 OXIDE; IODINATED HYDROCARBON; ORGANOMETALLIC COMPOUND; PYRIDINE DERIVATIVE; PYRIDINE N-OXIDE;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CONTROLLED STUDY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHEMISTRY;

AMIDES; CATALYSIS; HYDROCARBONS, IODINATED; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PYRIDINES;

EID: 84928902581     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00489     Document Type: Article

References (53)

1. Ackermann, L. Acc. Chem. Res. 2014, 47, 281
2. Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731
3. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879
4. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
5. Cai, X.; Xie, B. Synthesis 2015, 47, 737 and references herein
6. Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685
7. Chaumontet, M.; Piccardi, R.; Audic, N.; Hitce, J.; Peglion, J. L.; Clot, E.; Baudoin, O. J. Am. Chem. Soc. 2008, 130, 15157
8. Lafrance, M.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570
9. 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
10. Polukeev, A. V.; Marcos, R.; Ahlquist, M. S. G.; Wendt, O. F. Chem. Sci. 2015, 6, 2060
11. Mukai, C.; Ohta, Y.; Oura, Y.; Kawaguchi, Y.; Inagaki, F. J. Am. Chem. Soc. 2012, 134, 19580
12. Whited, M. T.; Grubbs, R. H. Acc. Chem. Res. 2009, 42, 1607
13. Girard, S. A.; Knauber, T.; Li, C. J. Angew. Chem., Int. Ed. 2014, 53, 74
14. Wang, D. H.; Wasa, M.; Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 7190
15. Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3680
16. Wasa, M.; Engle, K. M.; Yu, J. Q. J. Am. Chem. Soc. 2009, 131, 9886
17. Shang, R.; Ilies, L.; Matsumoto, A.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 6030
18. Nadres, E. T.; Santos, G. I. F.; Shabashov, D.; Daugulis, O. J. Org. Chem. 2013, 78, 9689
19. Pan, F.; Shen, P. X.; Zhang, L. S.; Wang, X.; Shi, Z. J. Org. Lett. 2013, 15, 4758
20. Wei, Y.; Tang, H.; Cong, X.; Rao, B.; Wu, C.; Zeng, X. Org. Lett. 2014, 16, 2248
21. Zhang, S.-Y.; He, G.; Nack, W. A.; Zhao, Y.; Li, Q.; Chen, G. J. Am. Chem. Soc. 2013, 135, 2124
22. He, G.; Chen, G. Angew. Chem., Int. Ed. 2011, 50, 5192
23. Cheng, T.; Yin, W.; Zhang, Y.; Zhang, Y.; Huang, Y. Org. Biomol. Chem. 2014, 12, 1405
24. Ju, L.; Yao, J.; Wu, Z.; Liu, Z.; Zhang, Y. J. Org. Chem. 2013, 78, 10821
25. Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965
26. Zhang, Q.; Chen, K.; Rao, W.; Zhang, Y.; Chen, F. J.; Shi, B.-F. Angew. Chem., Int. Ed. 2013, 52, 13588
27. Li, C.; Yano, T.; Ishida, N.; Murakami, M. Angew. Chem., Int. Ed. 2013, 52, 9801
28. Hull, K. L.; Lanni, E. L.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 14047
29. Oi, S.; Fukita, S.; Inoue, Y. Chem. Commun. 1998, 22, 2439
30. Liang, L. B.; Fu, S. M.; Lin, D.; Zhang, X. Q.; Deng, Y. F.; Jiang, H. F.; Zeng, W. J. Org. Chem. 2014, 79, 7492
31. Shibata, T.; Takayasu, S.; Yuzawa, S.; Otani, T. Org. Lett. 2012, 14, 5106
32. Tsai, C. C.; Shih, W. C.; Fang, C. H.; Li, C. Y.; Ong, T. G.; Yap, G. P. A. J. Am. Chem. Soc. 2010, 132, 11887
33. Karthikeyan, I.; Sekar, G. Eur. J. Org. Chem. 2014, 36, 8055
34. Xie, Y.; Chen, T.; Fu, S.; Li, X.; Deng, Y.; Jiang, H.; Zeng, W. Chem. Commun. 2014, 50, 10699
35. Li, M. Y.; Xie, Y.; Ye, Y.; Zou, Y.; Jiang, H. F.; Zeng, W. Org. Lett. 2014, 16, 6232
36. Xiao, B.; Liu, Z. J.; Liu, L.; Fu, Y. J. Am. Chem. Soc. 2013, 135, 616
37. Cho, S. H.; Hwang, S. J.; Chang, S. J. Am. Chem. Soc. 2008, 130, 9254
38. Wu, J.; Cui, X.; Chen, L.; Jiang, G.; Wu, Y. J. Am. Chem. Soc. 2009, 131, 13888
39. Tan, Y.; Barrios-Landeros, F.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 3683
40. Duric, S.; Sypaseuth, F. D.; Hoof, S.; Svensson, E.; Tzschucke, C. C. Chem.-Eur. J. 2013, 19, 17456
41. Campeau, L. C.; Stuart, D. R.; Leclerc, J. P.; Bertrand-Laperle, M.; Villemure, E.; Sun, H. Y.; Lasserre, S.; Guimond, N.; Lecavallier, M.; Fagnou, K. J. Am. Chem. Soc. 2009, 131, 3291
42. Hao, X. Q.; Chen, L. J.; Ren, B.; Li, L. Y.; Yang, X. Y.; Gong, J. F.; Niu, J. L.; Song, M. P. Org. Lett. 2014, 16, 1104
43. Zhang, L. B.; Hao, X. Q.; Zhang, S. K.; Liu, K.; Ren, B.; Gong, J. F.; Niu, J. L.; Song, M. P. J. Org. Chem. 2014, 79, 10399
44. It is also worth noting that employing phenylboronic acid as aryl sources instead of iodobenzene 2c could not lead to the formation of desired arylation products including 3-1a and 3-aa.
45. 1H NMR spectrum about Pd(II) intermediate B, please see SI for more details.
46. Chiong, H. A.; Pham, Q.-N.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 9879
47. Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154
48. García-Barrantes, P. M.; Feliciano, A. S. Eur. J. Med. Chem. 2013, 70, 548
49. Aksinenko, A. Y.; Sokolov, V. B. J. Fluor. Chem. 2012, 137, 105
50. Kokatla, H. P.; Lakshman, M. K. J. Org. Chem. 2011, 76, 7842
51. Wang, C. Y.; Song, R. J.; Wei, W. T.; Fan, J. H.; Li, J. H. Chem. Commun. 2015, 51, 2361
52. Hay, D. A.; Brennan, P. E. J. Am. Chem. Soc. 2014, 136, 9308
53. Stoermer, R.; Stroh, H.; Albert, H. Ber. Dtsch. Chem. Ges. 1935, 68B, 2102