Silver-catalyzed difunctionalization of terminal alkynes: Highly regio- and stereoselective synthesis of (Z)-β-Haloenol acetates

Organic Letters

Volumn 12, Issue 14, 2010, Pages 3262-3265

  Chen, Zhengwang ^a   Li, Jinghao ^a   Jiang, Huanfeng ^a   Zhu, Shifa ^a   Li, Yibiao ^a   Qi, Chaorong ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77954560873     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101251n     Document Type: Article

References (53)

1. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127
2. Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Chem. Rev. 2005, 105, 2329
3. Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082
4. Johnson, J. B.; Rovis, T. Angew. Chem., Int. Ed. 2008, 47, 840
5. Li, Y.; Liu, X.; Jiang, H.; Feng, Z. Angew. Chem., Int. Ed. 2010, 49, 3338
6. Minami, Y.; Kuniyasu, H.; Miyafuji, K.; Kambe, N. Chem. Commun. 2009, 3080
7. Beletskaya, I.; Moberg, C. Chem. Rev. 2006, 106, 2320
8. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079
9. Willis, M. C. Chem. Rev. 2010, 110, 725
10. For recent selected examples of difunctionalization of terminal alkyne, see
11. Goossen, L. J.; Rodríguez, N.; Goossen, K. Angew. Chem., Int. Ed. 2009, 48, 9592
12. Mizuno, A.; Kusama, H.; Iwasawa, N. Angew. Chem., Int. Ed. 2009, 48, 8318
13. Sha, F.; Huang, X. Angew. Chem., Int. Ed. 2009, 48, 3458
14. Ye, L.; Cui, L.; Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 3258
15. Dutta, B.; Gilboa, N.; Marek, I. J. Am. Chem. Soc. 2010, 132, 5588
16. Zhang, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 28
17. Kuang, J.; Ma, S. J. Am. Chem. Soc. 2010, 132, 1786
18. For recent selected examples, see
19. Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651
20. Cahiez, G.; Moyeux, A. Chem. Rev. 2010, 110, 1435
21. Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314
22. Bettinger, H. F.; Filthaus, M. J. Org. Chem. 2007, 72, 9750
23. Uchiyama, M.; Furuyama, T.; Kobayashi, M.; Matsumoto, Y.; Tanaka, K. J. Am. Chem. Soc. 2006, 128, 8404
24. Boukouvalas, J.; Loach, R. P. J. Org. Chem. 2008, 73, 8109
25. For selected examples, see
26. Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507
27. Goossen, L. J.; Paetzold, J. Angew. Chem., Int. Ed. 2004, 43, 1095
28. Zhang, D.; Ready, J. M. Org. Lett. 2005, 7, 5681
29. DeBergh, J. R.; Spivey, K. M.; Ready, J. M. J. Am. Chem. Soc. 2008, 130, 7828
30. Tang, W.; Liu, D.; Zhang, X. Org. Lett. 2003, 5, 205
31. β-Haloenol acetates are known to be effective precursors of α-keto dianions; see
32. Kowalski, C. J.; Haque, M. S. J. Org. Chem. 1985, 50, 5140
33. Kowalski, C. J.; O'Dowd, M. L.; Burke, M. C.; Fields, K. W. J. Am. Chem. Soc. 1980, 102, 5411
34. Kowalski, C. J.; Haque, M. S.; Fields, K. W. J. Am. Chem. Soc. 1985, 107, 1429
35. Pincock, J. A.; Yates, K. Can. J. Chem. 1970, 48, 3332
36. Barluenga, J.; Rodríguez, M. A.; Campos, P. J. J. Org. Chem. 1990, 55, 3104
37. Naodovic, M.; Yamamoto, H. Chem. Rev. 2008, 108, 3132
38. Yamamoto, Y. Chem. Rev. 2008, 108, 3199
39. Ding, Q.; Wu, J. J. Comb. Chem. 2008, 10, 541
40. Yoshida, S.; Fukui, K.; Kikuchi, S.; Yamada, T. J. Am. Chem. Soc. 2010, 132, 4072
41. Oh, C. H.; Karmakar, S.; Park, H.; Ahn, Y.; Kim, J. W. J. Am. Chem. Soc. 2010, 132, 1792
42. Luo, Y.; Li, Z.; Li, C.-J. Org. Lett. 2005, 7, 2675
43. Liu, W.; Jiang, H.; Huang, L. Org. Lett. 2010, 12, 312
44. Cao, H.; Jiang, H.; Mai, R.; Zhu, S.; Qi, C. Adv. Synth. Catal. 2010, 352, 143
45. Jiang, H.-F.; Zhao, J.-W. Tetrahedron Lett. 2009, 50, 60
46. Kowalski, C. J.; Haque, M. S. J. Org. Chem. 1985, 50, 5140
47. Kowalski, C. J.; Reddy, R. E. J. Org. Chem. 1992, 57, 7194
48. Zhu, N.; Hu, W.; Han, S.; Wang, Q.; Zhao, D. Org. Lett. 2008, 10, 4283
49. For representative preparation bromoalkynes from terminal alkynes with silver as the catalyst, see
50. Mu, Z.; Shu, L.; Fuchs, H.; Mayor, M.; Chi, L. J. Am. Chem. Soc. 2008, 130, 10840
51. Nie, X.; Wang, G. J. Org. Chem. 2006, 71, 4734
52. Ishino, Y.; Nishiguchi, I.; Nakao, S.; Hirashima, T. Chem. Lett. 1981, 641
53. Lewandos, G. S.; Maki, J. W.; Ginnebaugh, J. P. Organometallics 1982, 1, 1700