Beyond directed ortho metalation: Ru-catalyzed CAr-O activation/cross-coupling reaction by amide chelation

Journal of the American Chemical Society

Volumn 136, Issue 32, 2014, Pages 11224-11227

  Zhao, Yigang ^a   Snieckus, Victor ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; SYNTHESIS (CHEMICAL);

COUPLING PROCESS; COUPLING REACTION; CROSS-COUPLINGS; CRYOGENIC TEMPERATURES; DIRECTED ORTHO METALATION; DIRECTING GROUPS; GENERAL METHODOLOGIES; SUZUKI-MIYAURA REACTION;

CHEMICAL ACTIVATION;

3 METHOXYBENZAMIDE;

ARTICLE; CATALYSIS; CHELATION; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; SYNTHESIS;

EID: 84906082558     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja503819x     Document Type: Article

References (47)

1. de Meijere, A.; Brase, S.; Oestreich, M. Metal-Catalyzed Cross-Coupling Reactions and More; Wiley-VCH: Weinheim, 2014.
2. Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236
3. Seechurn, C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062
4. Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177
5. Yu, J.-Q.; Shi, Z.-J. Top. Curr. Chem. 2010, 292, 1
6. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
7. Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722
8. Negishi, E. I. Angew. Chem., Int. Ed. 2011, 50, 6738
9. Knappke, C. E. I.; Jacobi von Wangelin, A. Chem. Soc. Rev. 2011, 40, 4948
10. Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704
11. Nakao, Y.; Hiyama, T. Chem. Soc. Rev. 2011, 40, 4893
12. Oestreich, M., Ed. The Mizoroki-Heck Reaction; Wiley-VCH: Weinheim, 2009.
13. Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874
14. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529
15. Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826
16. Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698
17. Kakiuchi, F.; Matsuura, Y.; Kan, S.; Chatani, N. J. Am. Chem. Soc. 2005, 127, 5936
18. Wenkert, E.; Michelotti, E. L.; Swindell, C. S. J. Am. Chem. Soc. 1979, 101, 2246
19. Wenkert, E.; Michelotti, E. L.; Swindell, C. S.; Tingoli, M. J. Org. Chem. 1984, 49, 4894
20. Tobisu, M.; Shimasaki, T.; Chatani, N. Angew. Chem., Int. Ed. 2008, 47, 4866
21. Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A. M.; Garg, N. K.; Percec, V. Chem. Rev. 2011, 111, 1346
22. Yu, D. G.; Li, B. J.; Shi, Z.-J. Acc. Chem. Res. 2010, 43, 1486
23. Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2004, 126, 2706
24. Ueno, S.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2007, 129, 6098
25. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255
26. Ueno, S.; Mizushima, E.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2006, 128, 16516
27. Snieckus, V.; Macklin, T. In Handbook of C-H Transformations; Dyker, G., Ed.; Wiley: Weinheim, 2005; Vol. 1, p 106.
28. Hartung, C. G.; Snieckus, V. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley: Weinheim, 2002; p 330.
29. Snieckus, V. Chem. Rev. 1990, 90, 879
30. Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206
31. Snieckus, V.; Anctil, E. J. G. In Metal-Catalyzed Cross-Coupling Reactions and More; de Meijere, A.; Brase, S.; Oestreich, M., Eds.; Wiley: Weinheim, 2014; Vol. 3, p 1067
32. Board, J.; Cosman, J. L.; Rantanen, T.; Singh, S. P.; Snieckus, V. Platinum Metals Rev. 2013, 57, 234
33. Anctil, E. J. G.; Snieckus, V. J. Organomet. Chem. 2002, 653, 150
34. Zhao, Y.; Snieckus, V. Org. Lett. 2014, 16, 390-393
35. Zhao, Y.; Snieckus, V. U.S. Patent 8,168,833, 2012.
36. Larock, R. C. Comprehensive Organic Transformations. A Guide to Functional Group Preparations, 2 nd ed.; Wiley: New York, 2010.
37. Wencel-Delord, J.; Nimphius, C.; Wang, H. G.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 13001
38. Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 5286
39. Kaye, G. W. C.; Laby, T. H. Tables of Physical and Chemical Constants, 16 th ed.; Longman: New York, 1995.
40. Beak, P.; Brown, R. A. J. Org. Chem. 1982, 47, 34
41. Ludt, R. E.; Griffiths, J. S.; McGrath, K. N.; Hauser, C. R. J. Org. Chem. 1973, 38, 1668
42. Ueno, S.; Kochi, T.; Chatani, N.; Kakiuchi, F. Org. Lett. 2009, 11, 855
43. A study was carried out in analogous C-N activation/cross-coupling of anthranilamides which shows that comparable high yields can be obtained at 110 °C but with requirement of prolonged reaction times and that yields are greatly reduced at 80 °C even after much longer reaction times, see: Zhao, Y. Ph.D. Thesis, Queens Univesity, Kingston, Ontario, Canada, 2010.
44. Wang, Q. W.; Mayer, M. F.; Brennan, C.; Yang, F. K.; Hossain, M. M.; Grubisha, D. S.; Bennett, D. Tetrahedron 2000, 56, 4881
45. Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2009, 48, 3565
46. Antoft-Finch, A.; Blackburn, T.; Snieckus, V. J. Am. Chem. Soc. 2009, 131, 17750
47. Hurst, T. E.; Macklin, T. K.; Becker, M.; Hartmann, E.; Kuegel, W.; Parisienne-La Salle, J.-C.; Batsanov, A. S.; Marder, T. B.; Snieckus, V. Chem.-Eur. J. 2010, 16, 8155