Microwave-assisted decarboxylative three-component coupling of a 2-oxoacetic acid, an amine, and an alkyne

Journal of Organic Chemistry

Volumn 76, Issue 18, 2011, Pages 7608-7613

  Feng, Huangdi ^a,b   Ermolat'Ev, Denis S ^a   Song, Gonghua ^b   Van Der Eycken, Erik V ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC AMOUNTS; COPPER CATALYST; MICROWAVE-ASSISTED; MULTI-COMPONENT COUPLING; PROPARGYLAMINES; THREE-COMPONENT COUPLING;

ORGANIC COMPOUNDS;

ACETYLENE;

ACETIC ACID DERIVATIVE; ALKYNE; AMINE; COPPER;

ARTICLE; CATALYSIS; CATALYST; DECARBOXYLATION; MICROWAVE IRRADIATION; QUANTUM YIELD; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

EID: 80052780077     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2013725     Document Type: Article

References (58)

1. Kauffman, G. S.; Harris, G. D.; Dorow, R. L.; Stone, B. R. P.; Parsons, R. L.; Pesti, J. A.; Magnus, N. A.; Fortunak, J. M.; Confalone, P. N.; Nugent, W. A. Org. Lett. 2000, 2, 3119
2. Miura, M.; Enna, M.; Okuro, K.; Nomura, M. J. Org. Chem. 1995, 60, 4999
3. Nilsson, B.; Vargas, H. M.; Ringdahl, B.; Hacksell, U. J. Med. Chem. 1992, 35, 285
4. Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698
5. Angew. Chem. 1999, 111, 1808.
6. Hattoi, K.; Miyata, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 1151
7. Ermolat'ev, D. S.; Bariwal, J. B.; Steenackers, H. P. L.; De Keersmaecker, S. C. J.; Van der Eycken, E. V. Angew. Chem., Int. Ed. 2010, 49, 9465
8. Angew. Chem. 2010, 122, 9655.
9. Moura-Lettsa, G.; DiBlasi, C. M.; Bauer, R. A.; Tan, D. S. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 6745
10. Wakefield, J. Organolithium Methods in Organic Synthesis; Academic Press: London, 1988; p 32.
11. Wakefield, B. J. Organomagnesium Methods in Organic Synthesis; Academic Press: London, 1995; p 46.
12. Ding, C. H.; Chen, D. D.; Luo, Z. B.; Dai, L. X.; Hou, X. L. Synlett 2006, 1272
13. Harada, T.; Fujiwara, T.; Iwazaki, K.; Oku, A. Org. Lett. 2000, 2, 1855
14. Murai, T.; Mutoh, Y.; Ohta, Y.; Murakami, M. J. Am. Chem. Soc. 2004, 126, 5968
15. Zeng, T. Q.; Chen, W. W.; Cirtiu, C. M.; Moores, A.; Song, G. H.; Li, C. J. Green Chem. 2010, 12, 570
16. Abahmane, L.; Kohler, J. M.; Gross, G. A. Chem.-Eur. J. 2011, 17, 3005
17. Wei, C.; Li, Z.; Li, C. Org. Lett. 2003, 5, 4473
18. Chng, L. L.; Yang, J.; Wei, Y. F.; Y. Yinga, J. Y. Adv. Synth. Catal. 2009, 351, 2887
19. Zhang, X.; Corma, A. Angew. Chem., Int. Ed. 2008, 47, 4358
20. Angew. Chem. 2008, 120, 4430.
21. Huang, B.; Yao, X.; Li, C. J. Adv. Synth. Catal. 2006, 348, 1528
22. Li, P.; Zhang, Y.; Wang, L. Chem.-Eur. J. 2009, 15, 2045
23. Aschwanden, P.; Stephenson, C. R. J.; Carreira, E. M. Org. Lett. 2006, 8, 2437
24. Lo, V. K. Y.; Liu, Y.; Wong, M. K.; Che, C. M. Org. Lett. 2006, 8, 1529
25. Fassler, R.; Frantz, D. E.; Oetiker, J.; Carreira, E. M. Angew. Chem., Int. Ed. 2002, 41, 3054
26. Angew. Chem. 2002, 114, 3180.
27. Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763
28. Angew. Chem. 2003, 115, 4951.
29. Namitharan, K.; Pitchumani, K. Eur. J. Org. Chem. 2010, 411
30. Wei, C.; Zhang, L.; Li, C. J. Synlett 2004, 1472
31. Zani, L.; Bolm, C. Chem. Commun. 2006, 4263
32. Aguilar, D.; Contel, M.; Urriolabeitia, E. P. Chem.-Eur. J. 2010, 16, 9287
33. Yu, D. Y.; Zhang, Y. G. Adv. Synth. Catal. 2011, 353, 163
34. Li, Z.; Li, C. J. J. Am. Chem. Soc. 2004, 126, 11810
35. Scheuermann, C. J. Chem. Asian J. 2010, 5, 436
36. Zhang, C.; Seidel, D. J. Am. Chem. Soc. 2010, 132, 1798
37. Bi, H. P.; Zhao, L.; Liang, Y. M.; Li, C. J. Angew. Chem., Int. Ed. 2009, 48, 792
38. Angew. Chem. 2009, 121, 806.
39. Pereshivko, O. P.; Peshkov, V. A.; Van der Eycken, E. V. Org. Lett. 2010, 12, 2638
40. Bariwal, J. B.; Ermolat'ev, D. S.; Van der Eycken, E. V. Chem.-Eur. J. 2010, 16, 3281
41. Goossen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662
42. Becht, J. M.; Catala, C.; Drian, C. L.; Wagner, A. Org. Lett. 2007, 9, 1781
43. Bilodeau, F.; Brochu, M. C.; Guimond, N.; Thesen, K. H.; Forgione, P. J. Org. Chem. 2010, 75, 1550
44. Goossen, L. J.; Rodríguez, N.; Lange, P. P.; Linder, C. Angew. Chem., Int. Ed. 2010, 49, 1111
45. Angew. Chem. 2010, 122, 1129.
46. Park, A.; Park, K.; Kim, Y.; Sunwoo Lee, S. Org. Lett. 2011, 13, 944
47. Zhang, C.; Das, D.; Seidel., D. Chem. Sci. 2011, 2, 233
48. Zhang, F.; Greaney, M. F. Org. Lett. 2010, 12, 4745
49. Weaver, J. D.; Recio, A., III; Grenning, A. J.; Tung, J. A. Chem. Rev. 2011, 111, 1846
50. Goossen, L. J.; Rudolphi, F.; Oppel, C.; Rodríguez, N. Angew. Chem., Int. Ed. 2008, 47, 3043
51. Angew. Chem. 2008, 120, 3285.
52. Fang, P.; Li, M. Z.; Ge, H. B. J. Am. Chem. Soc. 2010, 132, 11898
53. Li, M. Z.; Ge, H. B. Org. Lett. 2010, 12, 3464
54. Rudolphi, F.; Song, B. R.; Goossen, L. J. Adv. Synth. Catal. 2011, 353, 337
55. Giles, R. L.; Sullivan, J. D. S; Steiner, A. M.; Looper, R. E. Angew. Chem. 2009, 121, 3162
56. Angew. Chem., Int. Ed. 2009, 48, 3116.
57. Yadav, J. S.; Reddy, B. V. S.; Naveenkumar, V.; Rao, R. S.; Nagaiah, K. New J. Chem. 2004, 28, 335
58. Wei, C.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584