C-H activation by amide chelation control: Ruthenium-catalyzed direct synthesis of 2-Aryl-3-furanamides

Advanced Synthesis and Catalysis

Volumn 356, Issue 7, 2014, Pages 1527-1532

  Zhao, Yigang ^a   Snieckus, Victor ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

amides; C H activation; chelation control; cross coupling; furans; ruthenium

Indexed keywords

EID: 84900397998     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201400147     Document Type: Article

References (35)

1. J. Wencel-Delord, F. Glorius, Nature Chem. 2013, 5, 369-375
2. R. G. Bergman, Nature 2007, 446, 391-393; for specialized reviews on C-H activation, see
3. N. Kuhl, M. N. Hopkinson, J. Wencel-Delord, F. Glorius, Angew. Chem. 2012, 124, 10382-10401
4. Angew. Chem. Int. Ed. 2012, 51, 10236-10254
5. J.-Q. Yu, Z. J. Shi, Top. Curr. Chem. 2010, 292, 1-378
6. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174-238; for reviews on C-O activation, see
7. B. J. Li, D. G. Yu, C. L. Sun, Z. J. Shi, Chem. Eur. J. 2011, 17, 1728-1759
8. B. M. Rosen, K. W. Quasdorf, D. A. Wilson, N. Zhang, A. M. Resmerita, N. K. Garg, V. Percec, Chem. Rev. 2011, 111, 1346-1416
9. D. G. Yu, B. J. Li, Z. J. Shi, Acc. Chem. Res. 2010, 43, 1486-1495.
10. F. Kakiuchi, M. Usui, S. Ueno, N. Chatani, S. Murai, J. Am. Chem. Soc. 2004, 126, 2706-2707
11. S. Ueno, E. Mizushima, N. Chatani, F. Kakiuchi, J. Am. Chem. Soc. 2006, 128, 16516-16517
12. S. Ueno, N. Chatani, F. Kakiuchi, J. Am. Chem. Soc. 2007, 129, 6098-6099
13. T. Koreeda, T. Kochi, F. Kakiuchi, J. Am. Chem. Soc. 2009, 131, 7238-7239.
14. J. C. Board, T. Rantanen, S. P. Singh, V. Snieckus, Platinum Met. Rev. 2013, 57, 234-258
15. V. Snieckus, E. J. G. Anctil, in: Metal-Catalyzed Cross-Coupling Reactions and More, Vol. 3, (Eds.:, A. de-Meijere, S. Bräse, M. Oestreich,), Wiley-VCH, Weinheim, 2014, pp- 1067-1134
16. V. Snieckus, T. Macklin, in: Handbook of C-H Transformations, Vol. 1, (Ed.:, G. Dyker,), Wiley-VCH, Weinheim, 2005, pp- 106-118, 262-264
17. C. G. Hartung, V. Snieckus, in: Modern Arene Chemistry, (Ed.:, D. Astruc,), Wiley-VCH, Weinheim, 2002, pp- 330-367
18. M. C. Whisler, S. MacNeil, V. Snieckus, P. Beak, Angew. Chem. 2004, 116, 2256-2276
19. Angew. Chem. Int. Ed. 2004, 43, 2206-2225.
20. F. Kakiuchi, S. Kan, K. Igi, N. Chatani, S. Murai, J. Am. Chem. Soc. 2003, 125, 1698-1699
21. F. Kakiuchi, Y. Matsuura, S. Kan, N. Chatani, J. Am. Chem. Soc. 2005, 127, 5936-5945.
22. G. W. C. Kaye, T. H. Laby, Tables of Physical and Chemical Constants, 16 th edn., Longman, New York, 1995.
23. Y. Zhao, Ph.D. Thesis, Queen's University, Kingston, ON, Canada, 2010
24. S. J. Blanksby, G. B. Ellison, Acc. Chem. Res. 2003, 36, 255-263
25. C. Barckholtz, T. A. Barckholtz, C. M. Hadad, J. Am. Chem. Soc. 1999, 121, 491-500.
26. C. A. Fleckenstein, H. Plenio, J. Org. Chem. 2008, 73, 3236-3244
27. K. Billingsley, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3358-3366.
28. K. B. Wiberg, Acc. Chem. Res. 1996, 29, 229-234.
29. Q. W. Wang, M. F. Mayer, C. Brennan, F. K. Yang, M. M. Hossain, D. S. Grubisha, D. Bennett, Tetrahedron 2000, 56, 4881-4891.
30. M. A. F. Brandao, A. B. Deoliveira, V. Snieckus, Tetrahedron Lett. 1993, 34, 2437-2440.
31. N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59.
32. T. T. Wang, J. Liu, Z. L. Lv, H. Y. Zhong, H. Chen, C. J. Niu, K. Li, Tetrahedron 2011, 67, 3476-3482
33. Y. Z. Dong, K. Nakagawa-Goto, C. Y. Lai, Y. Kim, S. L. Morris-Natschke, E. Lee, K. F. Bastow, K. H. Lee, Bioorg. Med. Chem. Lett. 2011, 21, 52-57
34. Y. Z. Dong, Q. Shi, H. C. Pai, C. Y. Peng, S. L. Pan, C. M. Teng, K. Nakagawa-Goto, D. L. Yu, Y. N. Liu, P. C. Wu, K. F. Bastow, S. L. Morris-Natschke, A. Brossi, J. Y. Lang, J. L. Hsu, M. C. Hung, E. Lee, K. H. Lee, J. Med. Chem. 2010, 53, 2299-2308.
35. 2 to the corresponding aldehyde is representative of useful 3,4-disubstituted functionalized furans which require multistep syntheses, see:, Y. Zhao, V. Snieckus, Org. Lett. 2014, 16, 390-393.