Cu(I)-catalyzed cross-coupling of conjugated ene-yne-ketones and terminal alkynes: Synthesis of furan-substituted allenes

Organic Letters

Volumn 16, Issue 16, 2014, Pages 4082-4085

  Hu, Fangdong ^a,b   Xia, Ying ^b   Ma, Chen ^a   Zhang, Yan ^b   Wang, Jianbo ^b  

^a SHANDONG UNIVERSITY   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84906212628     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501747f     Document Type: Article

References (55)

1. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091
2. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: New York, 1998.
3. Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861
4. Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577
5. Zhang, Y.; Wang, J. Eur. J. Org. Chem. 2011, 1015
6. Barluenga, J.; Valdés, C. Angew. Chem., Int. Ed. 2011, 50, 7486
7. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2012, 41, 560
8. Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236
9. Liu, Z.; Wang, J. J. Org. Chem. 2013, 78, 10024
10. Xiao, Q.; Xia, Y.; Li, H.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2011, 50, 1114
11. Hossain, M. L.; Ye, F.; Zhang, Y.; Wang, J. J. Org. Chem. 2013, 78, 1236
12. Ye, F.; Hossain, M. L.; Xu, Y.; Ma, X.; Xiao, Q.; Zhang, Y.; Wang, J. Chem. - Asian J. 2013, 8, 1404
13. Zhou, L.; Shi, Y.; Xiao, Q.; Liu, Y.; Ye, F.; Zhang, Y.; Wang, J. Org. Lett. 2011, 13, 968
14. Ye, F.; Shi, Y.; Zhou, L.; Xiao, Q.; Zhang, Y.; Wang, J. Org. Lett. 2011, 13, 5020
15. Miki, K.; Uemura, S.; Ohe, K. Chem. Lett. 2005, 34, 1068
16. Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410
17. Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260
18. Nishino, F.; Miki, K.; Kato, Y.; Ohe, K.; Uemura, S. Org. Lett. 2003, 5, 2615
19. Kato, Y.; Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. Org. Lett. 2003, 5, 2619
20. Miki, K.; Yokoi, T.; Nishino, F.; Kato, Y.; Washitake, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 2004, 69, 1557
21. Miki, K.; Washitake, Y.; Ohe, K.; Uemura, S. Angew. Chem., Int. Ed. 2004, 43, 1857
22. Vicente, R.; González, J.; Riesgo, L.; González, J.; López, L. A. Angew. Chem., Int. Ed. 2012, 51, 8063
23. González, J.; González, J.; Pérez-Calleja, C.; López, L. A.; Vicente, R. Angew. Chem., Int. Ed. 2013, 52, 5853
24. Cao, H.; Zhan, H.; Cen, J.; Lin, J.; Lin, Y.; Zhu, Q.; Fu, M.; Jiang, H. Org. Lett. 2013, 15, 1080
25. Zhan, H.; Lin, X.; Qiu, Y.; Du, Z.; Li, P.; Li, Y.; Cao, H. Eur. J. Org. Chem. 2013, 2284
26. Xia, Y.; Qu, S.; Xiao, Q.; Wang, Z.-X.; Qu, P.; Chen, Li.; Liu, Z.; Tian, L.; Huang, Z.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2013, 135, 13502
27. For a recent Rh(II)-catalyzed carbene transfer reaction of ene-yne-ketones with alkynes, see: González, M. J.; López, E.; Vicente, R. Chem. Commun. 2014, 50, 5379
28. For a detailed discussion on the effect of base on the transition-metal-catalyzed coupling reactions, see: Ouyang, K.; Xi, Z. Acta Chim. Sin. 2013, 71, 13
29. Wang, T.; Shi, S.; Hansmann, M. M.; Rettenmeier, E.; Rudolph, M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2014, 53, 3715
30. Wang, T.; Shi, S.; Rudolph, M.; Hashmi, A. S. K. Adv. Synth. Catal. 2014, 356, 2337
31. Modern Allene Chemistry; Krause, N.; Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vols. 1 and 2.
32. Ma, S. Palladium-Catalyzed Two- or Three-Component Cyclization of Functionalized Allenes. In Palladium in Organic Synthesis; Tsuji, J., Ed.; Springer: Berlin, 2005; pp 183-210.
33. Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Krause, N., Ed.; Georg Thieme Verlag: Stuttgart, 2008; Vol. 44 (Cumulenes and Allenes).
34. Hashmi, A. S. K. Angew. Chem., Int. Ed. 2000, 39, 3590
35. Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067
36. Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535
37. Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12
38. Ma, S. Acc. Chem. Res. 2003, 36, 701
39. Sydnes, L. K. Chem. Rev. 2003, 103, 1133
40. Tius, M. A. Acc. Chem. Res. 2003, 36, 284
41. Wei, L. L.; Xiong, H.; Hsung, R. P. Acc. Chem. Res. 2003, 36, 773
42. Brandsma, L.; Nedolya, N. A. Synthesis 2004, 735
43. Ma, S. Chem. Rev. 2005, 105, 2829
44. Ma, S. Aldrichimica Acta 2007, 40, 91
45. Brasholz, M.; Reissig, H.-U.; Zimmer, R. Acc. Chem. Res. 2009, 42, 45
46. Ma, S. Acc. Chem. Res. 2009, 42, 1679
47. Yu, S.; Ma, S. Angew. Chem., Int. Ed. 2012, 51, 3074
48. Yang, W.; Hashmi, A. S. K. Chem. Soc. Rev. 2014, 43, 2941
49. Hoffmann-Röder, A.; Krause, N. Angew. Chem., Int. Ed. 2004, 43, 1196
50. Kim, H.; Williams, L. J. Curr. Opin. Drug Discovery Dev. 2008, 11, 891
51. Krause, N.; Hoffmann-Röder, A. Tetrahedron 2004, 60, 11671
52. Brummond, K. M.; Deforrest, J. E. Synthesis 2007, 795
53. Ogasawara, M. Tetrahedron: Asymmetry 2009, 20, 259
54. Yu, S.; Ma, S. Chem. Commun. 2011, 47, 5384
55. Neff, R. K.; Frantz, D. E. ACS Catal. 2014, 4, 519