Gold(III)-catalyzed three-component coupling reaction (TCC) selective toward furans

Organic Letters

Volumn 15, Issue 11, 2013, Pages 2884-2887

  Li, Jian ^a   Liu, Li ^a   Ding, Dong ^a   Sun, Jiangtao ^a   Ji, Yangxuan ^a   Dong, Jialing ^a  

^a CHANGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84879247086     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401239j     Document Type: Article

References (47)

1. Katritzky, A. R. Comprehensive Heterocyclic Chemistry III; Elsevier: Amsterdam, 2008.
2. Pozharskii, A. F.; Katritzky, A. R.; Soldatenkov, A. T. Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications, 2 nd ed.; Wiley: Chichester, 2011.
3. Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076
4. Brown, R. C. D. Angew. Chem., Int. Ed. 2005, 44, 850
5. Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Org. Lett. 2001, 3, 3769
6. Sromek, A. W.; Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2005, 127, 10500
7. Suhre, M. H.; Reif, M.; Kirsch, S. F. Org. Lett. 2005, 7, 3873
8. Sniady, A.; Wheeler, K. A.; Dembinski, R. Org. Lett. 2005, 7, 1769
9. Zhang, J.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2006, 45, 6704
10. Zhou, C.-Y.; Chang, P. W. H.; Che, C.-M. Org. Lett. 2006, 8, 325
11. Zhang, Z.-P.; Cai, X.-B.; Wang, S.-P.; Yu, J.-L.; Liu, H.-J.; Cui, Y.-Y. J. Org. Chem. 2007, 72, 9838
12. Sniady, A.; Durham, A.; Morreale, M. S.; Wheeler, K. A.; Dembinski, R. Org. Lett. 2007, 9, 1175
13. Egi, M.; Azechi, K.; Akai, S. Org. Lett. 2009, 11, 5002
14. Aponick, A.; Li, C.-Y.; Malinge, J.; Marques, E. F. Org. Lett. 2009, 11, 4624
15. Blanc, A.; Tenbrink, K.; Weibel, J.-M.; Pale, P. J. Org. Chem. 2009, 74, 4360
16. Chen, Z.; Jiang, G.; Huang, H.; Pan, H. X. J. Org. Chem. 2011, 76, 1134
17. Huang, J. Y.; Kang, B.; Connell, T. J. Org. Chem. 2011, 76, 2379
18. Hashmi, A. S. K.; Yang, W.; Rominger, F. Angew. Chem., Int. Ed. 2011, 50, 5762
19. Chem.-Eur. J. 2012, 18, 6576.
20. Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285
21. Yao, T.; Zhang, X.; Larock, R. C. J. Org. Chem. 2005, 70, 7679
22. Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164
23. Zhou, C.-Y.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2006, 8, 325
24. Hashmi, A. S. K.; Sinha, P. Adv. Synth. Catal. 2004, 346, 432
25. Zhang, J.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2006, 45, 6704
26. Liu, Y.; Song, F.; Song, Z.; Liu, M.; Yan, B. Org. Lett. 2005, 7, 5409
27. Kramer, S.; Skrydstrup, T. Angew. Chem., Int. Ed. 2012, 51, 4681
28. Multicomponent Reactions; Zhu, J.; Bienaymé, H., Eds.; Wiley-VCH: Weinheim, 2005.
29. Posner, G. H. Chem. Rev. 1986, 86, 831
30. Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123
31. Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.-Eur. J. 2000, 6, 3321
32. Yan, B.; Liu, Y. Org. Lett. 2007, 9, 4323
33. Chernyak, N.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 2743
34. Chernyak, D.; Chernyak, N.; Gevorgyana, V. Adv. Synth. Catal. 2010, 352, 961
35. Zhang, Q.; Cheng, M.; Hu, X.; Li, B.-G.; Ji, J.-X. J. Am. Chem. Soc. 2010, 132, 7256
36. Phenylglyoxals can be synthesized from a terminal alkyne with pyridine- N -oxide via gold catalysis, which was used to deliver quinoxalines in one pot; see: Shi, S.; Wang, T.; Yang, W.; Rudolph, M.; Hashmi, A. S. K. Chem.-Eur. J. 2013, DOI: 10.1002/chem.201300518
37. Li, C.-J.; Wei, C. M. Chem. Commun 2002, 268
38. Wei, C. M.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473
39. Lo, V. K.-Y.; Kung, K. K.-Y.; Wong, M.-K.; Che, C.-M. J. Organomet. Chem. 2009, 694, 583
40. Zhang, X.; Corma, A. Angew. Chem. 2008, 120, 4430
41. Zhang, X.; Corma, A. Angew. Chem., Int. Ed. 2008, 47, 4358
42. Kidwai, M.; Bansal, V.; Kumarb, A.; Mozumdar, S. Green Chem. 2007, 9, 742
43. Huang, B.; Yao, X.; Li, C.-J. Adv. Synth. Catal. 2006, 348, 1528
44. Lo, V. K.-Y.; Liu, Y.; Wong, M.-K.; Che, C.-M. Org. Lett. 2006, 8, 1529
45. Elie, B. T.; Levine, C.; Ubarretxena-Belandia, I.; Varela-Ramírez, A.; Aguilera, R. J.; Ovalle, R.; Contel, M. Eur. J. Inorg. Chem. 2009, 3421
46. Hashmi, A. S. K. Angew. Chem., Int. Ed. 2010, 49, 5232
47. Wei, C. M.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584