Substitution of hydroxyl groups with alkynyl moieties using alkynylboron dihalides: An efficient approach to secondary alkylacetylene derivatives

Organic Letters

Volumn 8, Issue 5, 2006, Pages 879-881

  Kabalka, George W ^a   Yao, Min Liang ^a   Borella, Scott ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33644960321     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052957i     Document Type: Article

References (58)

1. Recent reviews: (a) Höger, S. Angew. Chem., Int. Ed. 2005, 44, 3806.
2. (b) Long, N. J.; Williams, C. K. Angew. Chem., Int. Ed. 2003, 42, 2586.
3. (c) Pieterse, K.; Lauritsen, A.; Schenning, A. P. H. J.; Vekemans, J. A. J. M.; Meijer, E. M. Chem. Eur. J. 2003, 9, 5597.
4. (d) Collings, J. C.; Parsons, A. C.; Porrès, L.; Beeby, A.; Batsanov, A. S.; Howard, J. A. K.; Lydon, D. P.; Low, P. J.; Fairlamb, I. J. S.; Marder, T. B. Chem. Commun. 2005, 2666.
5. (e) Hwang, G. T.; Son, H. S.; Ku, J. K.; Kim, B. H. J. Am. Chem. Soc. 2003, 125, 11241.
6. Recent reviews: (a) Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368.
7. (b) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935.
8. (c) Komdo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205.
9. (d) Suginome, M.; Ito, Y. Chem. Rev. 2000, 100, 3221.
10. (e) Smith, N. D.; Mancuso, J.; Lautens, M. Chem. Rev. 2000, 100, 3257.
11. (a) Chemistry and Biology of Naturally-Occurring Acetylenes and Related Compounds; Lam, J., Breteler, H., Arnsaon, T., Hansen, L., Eds.; Elsevier: Amsterdam, 1988.
12. (b) Lopez, S.; Fernández-Trillo, F.; Castedo, L.; Saá, C. Org. Lett. 2003, 5, 3725.
13. (c) Stütz, A.; Petranyi, G. J. Med. Chem. 1984, 27, 1539.
14. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
15. (b) Review: Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley: Weinheim, 1997; 203.
16. (c) Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566.
17. (a) Hierso, J.-C.; Fihri, A.; Amardeil, R.; Meunier, P.; Doucet, H.; Santelli, M.; Ivanov, V. V. Org. Lett. 2004, 6, 3473.
18. (b) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642.
19. (c) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729.
20. (d) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
21. (e) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679.
22. (f) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
23. (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
24. (b) Cui, D.-M.; Hashimoto, N.; Ikeda, S.-I, Sato, Y. J. Org. Chem. 1995, 60, 5752.
25. (a) Qian, M.; Negishi, E.-i. Tetrahedron Lett. 2005, 46, 2927.
26. (b) Anastasia, L.; Negishi, E.-i. Org. Lett. 2001, 3, 3111.
27. (a) Yang, L.-M.; Huang, L.-F.; Luh, T.-Y. Org. Lett. 2004, 6, 1461.
28. (b) Negishi, E.-i.; Zhang, Y.; Cederbaum, F. E.; Webb, M. B. J. Org. Chem. 1986, 51, 4080.
29. (c) Dang, H. P.; Linstrumelle, G. Tetrahedron Lett. 1978, 191.
30. (a) Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287.
31. (b) Negishi, E.-i. Acc. Chem. Res. 1982, 15, 340.
32. (a) Molander, G. A.; Katona, B. W.; Machrouhi, F. J. Org. Chem. 2002, 67, 8416.
33. (b) Castanet, A.-S.; Colobert, F.; Schlama, T. Org. Lett. 2000, 2, 3559.
34. (c) Oh, C. H.; Jung, S. H. Tetrahedron Lett. 2000, 41, 8513.
35. (d) Soderquist, J. A.; Matos, K.; Rane, A.; Ramos, J. Tetrahedron Lett. 1995, 36, 2401.
36. (e) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165.
37. (a) Negishi, E.-i.; Anastasia, L. Chem. Rev. 2003, 103, 1979.
38. (a) Pérez, I.; Sestelo, J. P.; Sarandeses, L. A. J. Am. Chem. Soc. 2001, 123, 4155.
39. (b) Pérez, I.; Sestelo, J. P.; Sarandeses, L. A. Org. Lett. 1999, 1, 1267.
40. (a) Brandsma, L. Preparative Acetylenic Chemistry; Elsevier: New York, 1988.
41. (b) Nicholas, K. M.; Siegel, J. J. Am. Chem. Soc. 1985, 107, 4999.
42. (c) Marcuzzi, F.; Modena, G.; Melloni, G. J. Org. Chem. 1982, 47, 4577.
43. (a) March 's Advanced Organic Chemistry: Reactions, Mechanism, and Structure, 5th ed.; Smith, M. B., March, J., Eds.; Wiley Interscience: New York, 2001.
44. (b) Ma, S.; He, Q.; Zhang, X. J. Org. Chem. 2005, 70, 3336.
45. (c) Enomoto, M.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 4599.
46. (a) Kabalka, G. W.; Wu, Z.; Trotman, S. E.; Gao, X. Org. Lett. 2000, 2, 255.
47. (b) Kabalka, G. W.; Wu, Z. Tetrahedron Lett. 2000, 41, 579.
48. (c) Kabalka, G. W.; Wu, Z.; Ju, Y. Tetrahedron Lett. 2001, 42, 5793.
49. Kabalka, G. W.; Wu, Z.; Ju, Y. Org. Lett. 2002, 4, 1491.
50. (e) Kabalka, G. W.; Wu, Z.; Ju, Y. J. Organomet. Chem. 2003, 680 (1-2), 12.
51. (a) Kabalka, G. W.; Yao, M.-L.; Borella, S.; Wu, Z.-Z. Org. Lett. 2005, 7, 2865.
52. (b) Kabalka, G. W.; Yao, M.-L.; Borella, S.; Wu, Z.-Z. Chem. Commun. 2005, 2492.
53. (c) Kabalka, G. W.; Wu, Z.; Ju, Y. Org. Lett. 2004, 6, 3929.
54. Leung, S.-W.; Singleton, D. A. J. Org. Chem. 1997, 62, 1955.
55. A similar procedure to alkynylzinic derivatives has been reported by Negishi. See ref 7b.
56. 4. The solvent was removed in vacuo and the product purified by silica gel column chromatography using hexane as an eluent to provide 3a in 68% yield.
57. (a) Tietze, L. F. Chem. Rev. 1996, 96, 115.
58. (b) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195.