Triarylaminium salt-initiated aerobic double friedel-crafts reaction of glycine derivatives with indoles

Advanced Synthesis and Catalysis

Volumn 355, Issue 10, 2013, Pages 1911-1916

  Huo, Congde ^a   Wang, Cheng ^a   Sun, Chougu ^a   Jia, Xiaodong ^a   Wang, Xicun ^a   Chang, Wenju ^a   Wu, Mingxia ^a  

^a NORTHWEST NORMAL UNIVERSITY   (China)

Author keywords

aerobic conditions; Friedel Crafts alkylation; glycine derivatives; indoles; triarylaminium salts

Indexed keywords

EID: 84880840704     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201300276     Document Type: Article

References (45)

1. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
2. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
3. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
4. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
5. Angew. Chem. Int. Ed. 2009, 48, 5094
6. C.-J. Li, Acc. Chem. Res. 2009, 42, 335.
7. K. Alagiri, P. Devadig, K. R. Prabhu, Chem. Eur. J. 2012, 18, 5160
8. H. Richter, R. Fröhlich, C.-G. Daniliuc, O. G. Mancheño, Angew. Chem. 2012, 124, 8784
9. Angew. Chem. Int. Ed. 2012, 51, 8656
10. E. Boess, C. Schmitz, M. Klussmann, J. Am. Chem. Soc. 2012, 134, 5317
11. C. Dai, F. Meschini, J. M. R. Narayanam, C. R. J. Stephenson, J. Org. Chem. 2012, 77, 4425
12. D. B. Freeman, L. Furst, A. G. Condie, C. R. J. Stephenson, Org. lett. 2012, 14, 94
13. M. Rueping, S. Zhu, R. M. Koenigs, Chem. Commun. 2011, 47, 8679
14. O. Baslé, N. Borduas, P. Dubois, J. M. Chapuzet, T.-H. Chan, J. Lessard, C.-J. Li, Chem. Eur. J. 2010, 16, 8162
15. O. Baslé, C.-J. Li, Org. lett. 2008, 10, 3661
16. Z. Li, D. S. Bohle, C.-J. Li, Proc. Natl. Acad. Sci. USA 2006, 103, 8928
17. Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 6968.
18. L. Zhao, O. Baslé, C.-J. Li, Proc. Natl. Acad. Sci. USA 2009, 106, 4106
19. L. Zhao, C.-J. Li, Angew. Chem. 2008, 120, 7183
20. Angew. Chem. Int. Ed. 2008, 47, 7075
21. J. Xie, Z.-Z. Huang, Angew. Chem. 2010, 122, 10379
22. Angew. Chem. Int. Ed. 2010, 49, 10181
23. G. Zhang, Y. Zhang, R. Wang, Angew. Chem. 2011, 123, 10613
24. Angew. Chem. Int. Ed. 2011, 50, 10429
25. S. Zhu, M. Rueping, Chem. Commun. 2012, 48, 11960
26. H. Richter, O. G. Mancheño, Org. Lett. 2011, 13, 6066
27. P. Liu, Z. Wang, J. Lin, X. Hu, Eur. J. Org. Chem. 2012, 1583
28. X. Jia, F. Peng, C. Qing, C. Huo, X. Wang, Org. Lett. 2012, 14, 4030
29. Z. Q. Wang, M. Hu, X. C. Huang, L. B. Gong, Y. X. Xie, J. H. Li, J. Org. Chem. 2012, 77, 8705.
30. A. G. Griesbeck, N. Hoffmann, K. Warzecha, Acc. Chem. Res. 2007, 40, 128.
31. C. Huo, X. Xu, J. An, X. Jia, X. Wang, C. Wang, J. Org. Chem. 2012, 77, 8310
32. C. Huo, X. Xu, X. Jia, X. Wang, J. An, C. Sun, Tetrahedron 2012, 68, 190
33. C. Huo, J. An, X. Xu, X. Jia, X. Wang, L. Kang, Tetrahedron Lett. 2013, 54, 1145
34. C. Huo, C. Sun, D. Hu, X. Jia, X. Xu, Z. Liu, Tetrahedron Lett. 2011, 52, 7008
35. C. Huo, R. Wei, W. Zhang, L. Yang, Z. Liu, Synlett 2005, 161
36. C. Huo, X. Jia, W. Zhang, L. Yang, Z. Liu, Synlett 2004, 251
37. C. Huo, J. An, W. Chang, X. Jia, L. Kang, M. Wu, Tetrahedron 2013, 69, 6375.
38. M. Shiri, M. A. Zolfigol, H. G. Kruger, Z. Tanbakouchian, Chem. Rev. 2010, 110, 2250, and references cited therein.
39. M. Castanho, N. Santos, Peptide Drug Discovery and Development: Translational Research in Academia and Industry; Wiley-VCH, Weinheim, 2011, and references cited therein.
40. D. J. Bellville, D. W. Wirth, N. L. Bauld, J. Am. Chem. Soc. 1981, 103, 718
41. P. G. Gassman, D. A. Singleton, J. Am. Chem. Soc. 1984, 106, 7993
42. D. W. Reynolds, K. T. Lorenz, H.-S. Chiou, D. J. Bellville, R. A. Pabon, N. L. Bauld, J. Am. Chem. Soc. 1987, 109, 4960.
43. Distonic ions are chemical species that contain both a radical and an ionic site on different atoms of the same molecule. For a review see:, K. M. Stirk, L. K. M. Kiminkinen, H. I. Kenttamaa, Chem. Rev. 1992, 92, 1649.
44. It has been postulated that the stability of free radicals is enhanced by the presence at the radical center of both an electron-donating and an electron-withdrawing group. The effect arises from increased resonance. See:, M. B. Smith, J. March, Advanced Organic Chemistry, 6 th edn., John Wiley & Sons, Inc, New York, 2007, p 272.
45. H. Mayr, G. Lang, A. R. Ofial, J. Am. Chem. Soc. 2002, 124, 4076.