Efficient synthesis of aryl vinyl ethers exploiting 2,4,6- trivinylcyclotriboroxane as a vinylboronic acid equivalent

Journal of Organic Chemistry

Volumn 69, Issue 15, 2004, Pages 5087-5092

  McKinley, Neola F ^a   O'Shea, Donal F ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; COPPER COMPOUNDS; CRYSTAL STRUCTURE; ORGANOMETALLICS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

AMINE BASES; X RAY CRYSTAL STRUCTURE;

ETHERS;

2,4,6 TRIVINYLCYCLOTRIBOROXANE; ALKANE DERIVATIVE; BORONIC ACID DERIVATIVE; COPPER ACETATE; ETHER DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; LOW TEMPERATURE; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION OPTIMIZATION; ROOM TEMPERATURE; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 3543008949     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049314l     Document Type: Article

References (42)

1. (a) Kerins, F.; O'Shea, D. F. J. Org. Chem. 2002, 67, 4968.
2. (b) Matteson, D. S. J. Org. Chem. 1962, 27, 3712.
3. (c) Coleman, C. M.; O'Shea, D. F. J. Am. Chem. Soc. 2003, 125, 4054.
4. Kojima, K; Sawamoto, M.; Higashimura, T. Macromolecules 1989, 22, 1552.
5. (a) Savinov, S. N.; Austin, D. J. Chem. Commun. 1999, 1813.
6. (b) Marko, I. E.; Evans, G. R.; Declercq, J.-P. Tetrahedron 1994, 50, 4557.
7. (c) El-Nabi, H. A. A. Tetrahedron 1997, 53, 1813.
8. (a) Maligres, P. E.; Waters, M. M.; Lee, J.; Reamer, R. A.; Askin, D.; Ashwood, M. S.; Cameron, M. J. Org. Chem. 2002, 67, 1093.
9. (b) Wenkert, E.; Alonso, M. E.; Buckwalter, B. L.; Sanchez, E. L. J. Am. Chem. Soc. 1983, 105, 2021.
10. Lyle, F. R. U.S. Patent 5 973 257, 1985; Chem. Abstr. 1985, 65, 2870.
11. Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2003, 5, 1301.
12. Maligres, P. E.; Waters, M. M.; Lee, J.; Reamer, R. A.; Askin, D. J. Org. Chem. 2002, 67, 1093.
13. Reppe, W. Ann. 1956, 601, 84.
14. Okimoto, Y.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2002, 124, 1590.
15. Blouin, M.; Frenette R. J. Org. Chem. 2001, 66, 9043.
16. (a) Evans, D. A.; Katz, J. L.; West, T. R.; Tetrahedron Lett. 1998, 39, 2937.
17. (b) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933.
18. (c) Lam P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941.
19. (d) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415.
20. (e) Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 1381.
21. (f) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400 (review).
22. Lam, P. Y. S.; Vincent, G.; Bonne, D.; Clark, C. G. Tetrahedron Lett. 2003, 44, 4927.
23. Sagar, A. D.; Tale, R. H.; Adude, R. N. Tetrahedron Lett. 2003, 44, 7061.
24. (a) Burg, A. B. J. Am. Chem. Soc. 1940, 62, 2228.
25. (b) Snyder, H. R.; Konecky, M. S.; Lennarz, W. J. J. Am. Chem. Soc. 1958, 80, 3611.
26. (a) Beckmann, J.; Dakternieks, D.; Duthie, A.; Lim, A. E. K.; Tiekink, E. R. T. J. Organomet. Chem. 2001, 633, 149.
27. (b) Yalpani, M.; Boese, R. Chem. Ber. 1983, 116, 3347.
28. (c) Beckett, M. A.; Brassington, D. S.; Owen, P.; Hursthouse, M. B.; Light, M. E.; Malik, K. M. A.; Varma, K. S. J. Organomet. Chem. 1999, 585, 7.
29. (d) Beckett, M. A.; Strickland, G. C.; Varma, K. S.; Hibbs, D. E.; Hursthouse, M. B.; Malik, K. M. A. J. Organomet. Chem. 1997, 535, 33.
30. (e) Beckett, M. A.; Strickland, G. C.; Varma, K. S.; Hibbs, D. E.; Hursthouse, M. B.; Malik, K. M. A. Polyhedron 1995, 14, 2623.
31. (f) Ferguson, G.; Lough, A. J.; Sheehan, J. P.; Spalding, T. R. Acta Crystallogr. Sect. C 1990, 46, 2390.
32. (g) Yalpani, M.; Köster, R. Chem. Ber. 1988, 121, 1553.
33. (h) Das, M. K.; Mariategui, J. F.; Niedenzu, K. Inorg. Chem. 1987, 26, 3114.
34. (i) Wu, Q. G.; Wu, G.; Brancaleon, L.; Wang, S. Organometallics 1999, 18, 2553.
35. The possible in situ formation of triarylboroxines 4 has been proposed; see ref 11a.
36. Höpfl, H. J. Organomet. Chem. 1999, 581, 129.
37. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
38. (b) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972.
39. (c) Wright, S. W.; Hageman, D. L.; McClure, L. D. J. Org. Chem. 1994, 59, 6095.
40. (d) Matos, K.; Soderquist, J. A. J. Org. Chem. 1998, 63, 461.
41. (a) Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979.
42. (b) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260