CuI-catalyzed cross-coupling of N-tosylhydrazones with terminal alkynes: Synthesis of 1,3-disubstituted allenes

Journal of Organic Chemistry

Volumn 78, Issue 3, 2013, Pages 1236-1241

  Hossain, Mohammad Lokman ^a   Ye, Fei ^a   Zhang, Yan ^a   Wang, Jianbo ^a,b  

^a PEKING UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1-ALKYNES; ALLENES; CROSS-COUPLINGS; TERMINAL ALKYNE;

CATALYSIS; FUNCTIONAL GROUPS;

ACETYLENE;

ALKYNE; ALLENE DERIVATIVE; BASE; COPPER; FUNCTIONAL GROUP; HYDRAZONE DERIVATIVE; N TOSYLHYDRAZONE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; COLUMN CHROMATOGRAPHY; CROSS COUPLING REACTION; ONE POT SYNTHESIS; REACTION OPTIMIZATION; SYNTHESIS;

EID: 84873354347     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3024686     Document Type: Article

References (49)

1. Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vols. 1 and 2.
2. 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.
3. Tius, M. Acc. Chem. Res. 2003, 36, 284
4. Ma, S. Acc. Chem. Res. 2003, 36, 701
5. Wei, L. L.; Xiong, H.; Hsung, R. P. Acc. Chem. Res. 2003, 36, 773
6. Brandsma, L.; Nedolya, N. A. Synthesis 2004, 735
7. Ma, S. Chem. Rev. 2005, 105, 2829
8. Ma, S. Aldrichimica Acta 2007, 40, 91
9. Brasholz, M.; Reissig, H.-U.; Zimmer, R. Acc. Chem. Res. 2009, 42, 45
10. Ma, S. Acc. Chem. Res. 2009, 42, 1679
11. For reviews on allene units in natural products and pharmaceuticals, see: Hoffmann-Röder, A.; Krause, N. Angew. Chem., Int. Ed. 2004, 43, 1196
12. Krause, N.; Hoffmann-Röder, A. Tetrahedron 2004, 60, 11671
13. Brummond, K. M.; Deforrest, J. E. Synthesis 2007, 795
14. Ogasawara, M. Tetrahedron: Asymmetry 2009, 20, 259
15. Deutsch, C.; Lipshutz, B. H.; Krause, N. Angew. Chem., Int. Ed. 2007, 46, 1650
16. Pu, X.; Ready, J. M. J. Am. Chem. Soc. 2008, 130, 10874
17. Tang, M.; Fan, C.-A.; Zhang, F.-M.; Tu, Y.-Q.; Zhang, W.-X.; Wang, A.-X. Org. Lett. 2008, 10, 5585
18. Lo, V. K.-Y.; Wong, M.-K.; Che, C.-M. Org. Lett. 2008, 10, 517
19. Liu, H.; Leow, D.; Huang, K.-W.; Tan, C.-H. J. Am. Chem. Soc. 2009, 131, 1712
20. Ogasawara, M.; Okada, A.; Nakajima, K.; Takahashi, T. Org. Lett. 2009, 11, 177
21. Kolakowski, R. V.; Manpadi, M.; Zhang, Y.; Emge, T. J.; Williams, L. J. J. Am. Chem. Soc. 2009, 131, 12910
22. Zhao, X.; Zhong, Z.; Peng, P.; Zhang, W.; Wang, J. Chem. Commun. 2009, 2535
23. Bolte, B.; Odabachian, Y.; Gagosz, F. J. Am. Chem. Soc. 2010, 132, 7294
24. Lo, V. K.-Y.; Zhou, C.-Y.; Wong, M.-K.; Che, C.-M. Chem. Commun. 2010, 46, 213
25. Ahmed, M.; Arnuald, T.; Barrett, A. G. M.; Braddock, D. C.; Flack, K.; Procopiou, P. A. Org. Lett. 2000, 2, 551
26. Lavallo, V.; Frey, G. D.; Kouser, S.; Donnadieu, B.; Bertrand, G. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 13569
27. Rona, P.; Crabbé, P. J. Am. Chem. Soc. 1969, 91, 3289
28. Kuang, J.; Ma, S. J. Org. Chem. 2009, 74, 1763
29. Kuang, J.; Ma, S. J. Am. Chem. Soc. 2010, 132, 1786
30. Kuang, J.; Luo, H.; Ma, S. Adv. Synth. Catal. 2012, 354, 933
31. Ye, J.; Li, S.; Chen, B.; Fan, W.; Kuang, J.; Liu, J.; Liu, Y.; Miao, B.; Wan, B.; Wang, Y.; Xie, X.; Yu, Q.; Yuan, W.; Ma, S. Org. Lett. 2012, 14, 1346
32. Xiao, Q.; Xia, Y.; Li, H.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2011, 50, 1114
33. Jones, V. K.; Deutschman, A. J., Jr. J. Org. Chem. 1965, 30, 3978
34. Suárez, A.; Fu, G. C. Angew. Chem., Int. Ed. 2004, 43, 3580
35. Hassink, M.; Liu, X.; Fox, J. M. Org. Lett. 2011, 13, 2388
36. Mondal, S.; Nechab, M.; Campolo, D.; Vanthuyne, N.; Bertrand, M. P. Adv. Synth. Catal. 2012, 354, 1987
37. Zhang, Y.; Wang, J. Eur. J. Org. Chem. 2011, 1015
38. Barluenga, J.; Valdés, C. Angew. Chem., Int. Ed. 2011, 50, 7486
39. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2012, 41, 560
40. Elsevier, C. J.; Vermeer, P. J. Org. Chem. 1985, 50, 3042
41. Sato, I.; Matsueda, Y.; Kadowaki, K.; Yonekubo, S.; Shibata, T.; Soai, K. Helv. Chim. Acta 2002, 85, 3383
42. Yamashita, T.; Nishiguchi, T.; Kato, J.; Muroya, Y.; Katsumura, Y. J. Photopolym. Sci. Technol. 2005, 18, 95
43. Kim, S.; Cho, C. M.; Yoon, J.-Y. J. Org. Chem. 1996, 61, 6018
44. Oku, M.; Arai, S.; Katayama, K.; Shioiri, T. Synlett 2000, 5, 543
45. Van Rossum, A. J. G.; Nivard, R. J. F. J. Chem. Soc., Perkin Trans. 2 1976, 1322
46. Elsevier, C. J.; Vermeer, P. J. Org. Chem. 1989, 54, 3726
47. Satoh, T.; Hanaki, N.; Kuramuchi, Y.; Inoue, Y.; Hosoya, K.; Sakai, K. Tetrahedron 2002, 58, 2533
48. Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83
49. Warner, P.; Sutherland, R. J. Org. Chem. 1992, 57, 6294