Copper (I) iodide-catalyzed one-step preparation of functionalized allenes from terminal alkynes: Amine effect

Advanced Synthesis and Catalysis

Volumn 354, Issue 5, 2012, Pages 933-944

  Kuang, Jinqiang ^a   Luo, Hongwen ^a   Ma, Shengming ^a,b  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

amine effect; catalysis; copper(I) iodide; synthesis of allenes

Indexed keywords

EID: 84858760279     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100772     Document Type: Article

References (59)

1. K. K. Wang, Chem. Rev. 1996, 96, 207-222
2. J. A. Marshall, Chem. Rev. 2000, 100, 3163-3185
3. A. S. K. Hashmi, Angew. Chem. 2000, 112, 3737-3740
4. Angew. Chem. Int. Ed. 2000, 39, 3590-3593
5. R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067-3125
6. X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 2001, 34, 535-544
7. R. W. Bates, V. Satcharoen, Chem. Soc. Rev. 2002, 31, 12-21
8. S. Ma, Acc. Chem. Res. 2003, 36, 701-712
9. L. Brandsma, N. A. Nedolya, Synthesis 2004, 735-745
10. M. A. Tius, Acc. Chem. Res. 2003, 36, 284-290
11. L. L. Wei, H. Xiong, R. P. Hsung, Acc. Chem. Res. 2003, 36, 773-782
12. S. Ma, Palladium-Catalyzed Two- or Three-Component Cyclization of Functionalized Allenes in Palladium in Organic Synthesis, (Ed.:, J. Tsuji,), pp. 183-210, Springer, Berlin, Heidelberg, 2005
13. S. Ma, Chem. Rev. 2005, 105, 2829-2871
14. S. Ma, Aldrichimica Acta 2007, 40, 91-102
15. H. Kim, L. J. Williams, Curr. Opin. Drug Disc. Devel. 2008, 11, 870-894
16. M. Brasholz, H.-U. Reissig, R. Zimmer, Acc. Chem. Res. 2009, 42, 45-56
17. S. Ma, Acc. Chem. Res. 2009, 42, 1679-1688.
18. L. K. Sydnes, Chem. Rev. 2003, 103, 1133-1150
19. Modern Allene Chemistry, (Eds.:, N. Krause, A. S. K. Hashmi,), Vols. 1 and 2, Wiley-VCH, Weinheim, 2004
20. N. Krause, A. Hoffmann-Röder, Tetrahedron 2004, 60, 11671-11694
21. G. B. Hammond, ACS Symp. Ser. 2005, 911, 204-215
22. R. Saeeng, M. Isobe, Chem. Lett. 2006, 35, 552-557
23. K. M. Brummond, J. E. Deforrest, Synthesis 2007, 795-818
24. M. Ogasawara, Tetrahedron: Asymmetry 2009, 20, 259-271
25. S. Yu, S. Ma, Chem. Commun. 2011, 47, 5384-5418.
26. P. Crabbé, H. Fillion, D. André, J.-L. Luche, J. Chem. Soc. Chem. Commun. 1979, 859-860
27. S. Searles, Y. Li, B. Nassim, M-T. R. Lopes, P. T. Tran, P. Crabbé, J. Chem. Soc. Perkin Trans. 1 1984, 747-751
28. S. Ma, H. Hou, S. Zhao, G. Wang, Synthesis 2002, 1643-1645
29. U. Kazmaier, S. Lucas, M. Klein, J. Org. Chem. 2006, 71, 2429-2433.
30. J. Kuang, S. Ma, J. Org. Chem. 2009, 74, 1763-1765.
31. J. Kuang, S. Ma, J. Am. Chem. Soc. 2010, 132, 1786-1787.
32. H. Nakamura, T. Sugiishi, Y. Tanaka, Tetrahedron Lett. 2008, 49, 7230-7233.
33. For limited success on the CuI-catalyzed one-step synthesis of allenes in low yields (14-64%) from terminal alkynes and aldehydes under the irradiation of microwave, see:, S. Kitagaki, M Komizu, C. Mukai, Synlett 2011, 1129-1132. According to the reported examples, the tolerance of functional groups is also rather poor.
34. L.-I. Olsson, A. Claesson, Synthesis 1979, 743-745
35. S. S. Nikam, K. H. Chu, K. K. Wang, J. Org. Chem. 1986, 51, 745-747
36. J. A. Marshall, X.-J. Wang, J. Org. Chem. 1990, 55, 2995-2996
37. J. A. Marshall, K. G. Pinney, J. Org. Chem. 1993, 58, 7180-7184
38. J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968
39. S. Ma, W. Gao, Tetrahedron Lett. 2000, 41, 8933-8936
40. A. Hoffmann-Röder, N. Krause, Org. Lett. 2001, 3, 2537-2538
41. R. W. Friesen, M. Blouin, J. Org. Chem. 1993, 58, 1653-1654
42. S. Ma, S. Zhao, J. Am. Chem. Soc. 1999, 121, 7943-7944
43. C. Fu, J. Li, S. Ma, Chem. Commun. 2005, 4119-4121
44. J. Li, C. Fu, G. Chen, G. Chai, S. Ma, Adv. Synth. Catal. 2008, 350, 1376-1382
45. Y. Deng, X. Jin, S. Ma, J. Org. Chem. 2007, 72, 5901-5904
46. Y. Deng, Y. Yu, S. Ma, J. Org. Chem. 2008, 73, 585-589.
47. S. Ma, F. Yu, W. Gao, J. Org. Chem. 2003, 68, 5943-5949.
48. V. K. Y. Lo, M.-K. Wong, C.-M. Che, Org. Lett. 2008, 10, 517-519
49. V. K.-Y. Lo, C.-Y. Zhou, M.-K. Wong, C.-M. Che, Chem. Commun. 2010, 46, 213-215.
50. H. Nakamura, T. Kamakura, M. Ishikura, J.-F. Biellmann, J. Am. Chem. Soc. 2004, 126, 5958-5959
51. H. Nakamura, S. Tashiro, T. Kamakura, Tetrahedron Lett. 2005, 46, 8333-8336
52. H. Nakamura, S. Onagi, T. Kamakura, J. Org. Chem. 2005, 70, 2357-2360
53. H. Nakamura, S. Onagi, Tetrahedron Lett. 2006, 47, 2539-2542
54. H. Nakamura, T. Kamakura, S. Onagi, Org. Lett. 2006, 8, 2095-2098
55. H. Nakamura, M. Ishikura, T. Sugiishi, T. Kamakura, J.-F. Biellmann, Org. Biomol. Chem. 2008, 6, 1471-1477.
56. P. Crabbé, B. Nassim, M-T. R. Lopes, Org. Synth. 1985, 63, 203.
57. S. Redon, A.-L. B. Berkaoui, X. Pannecoucke, F. Outurquin, Tetrahedron 2007, 63, 3707-3717.
58. C. J. Elsevier, P. Vermeer, J. Org. Chem. 1989, 54, 3726-3730.
59. E. Yoneda, S. Zhang, D. Zhou, K. Onitsuka, S. Takahashi, J. Org. Chem. 2003, 68, 8571-8576.