Copper(II) acetate-catalyzed addition of arylboronic acids to aromatic aldehydes

Journal of Organic Chemistry

Volumn 74, Issue 2, 2009, Pages 943-945

  Zheng, Hanmei ^a   Zhang, Qiang ^a   Chen, Jiuxi ^a   Liu, Miaochang ^a   Cheng, Shuanghua ^a   Ding, Jinchang ^b   Wu, Huayue ^a   Su, Weike ^a,c  

^a WENZHOU UNIVERSITY   (China)

^b WENZHOU VOCATIONAL AND TECHNICAL COLLEGE   (China)

^c ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC ALDEHYDES; ARYLBORONIC ACIDS;

ACIDS; ALDEHYDES; AROMATIC COMPOUNDS; METHANOL;

COPPER;

ALDEHYDE; BENZENEBORONIC ACID; BORONIC ACID DERIVATIVE; COPPER ACETATE; LIGAND; METHANOL DERIVATIVE; SOLVENT; TOLUENE; METHANOL; ORGANOMETALLIC COMPOUND;

AIR; ARTICLE; CATALYSIS; ELECTRON TRANSPORT; LIGAND BINDING; MOISTURE; MOLECULAR INTERACTION; SUBSTITUTION REACTION; SYNTHESIS; CHEMISTRY;

ALDEHYDES; BORONIC ACIDS; CATALYSIS; LIGANDS; METHANOL; ORGANOMETALLIC COMPOUNDS; SOLVENTS;

EID: 60849117249     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802225j     Document Type: Article

References (44)

1. (a) Schmidt, F.; Stemmler, R. T.; Rudolph, J.; Bolm, C. Chem. Rev. 2006, 35, 454.
2. (b) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
3. (c) Bolm, C.; Hildebrand, J. P.; Muniz, K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40, 3284.
4. (d) Darses, S.; Genet, J. P. Eur. J. Org. Chem. 2003, 4313.
5. (a) Furstner, A. Chem. Rev. 1999, 99, 991.
6. (b) Boudier, A.; Bromm, L. O.; Bromm, L. M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414.
7. (c) Bolm, C.; Rudolph, J. J. Am. Chem. Soc. 2002, 124, 14850.
8. (d) Guijarro, D.; Yus, M. Tetrahedron. 2000, 56, 1135.
9. (e) Boymond, L.; Rottlander, M.; Cahiez, G.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 1701.
10. (f) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449.
11. (g) Lee, J. S.; Velarde, O. R.; Guijarro, A.; Wurst, J. R.; Rieke, R. D. J. Org. Chem. 2000, 65, 5428.
12. (h) Weber,B.; Seebach, D. Tetrahedron 1994, 50, 7473.
13. (i) Noyori, R.; Kitamura, M. Angew.Chem., Int. Ed. 1991, 30, 49.
14. (j) Dosa, P. I.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1997, 62, 444.
15. (k) Bolm, C.; Hermanns, N.; Hildebrand, J. P.; Muniz, K. Angew. Chem., Int. Ed. 2000, 39, 3465.
16. (l) Ogawa, Y.; Mori, M.; Saiga, A.;Takagi, K. Chem. Lett. 1996, 1069.
17. (m) Kondo, Y.; Takazawa, N.; Yamazaki, C.; Sakamoto, T. J. Org. Chem. 1994, 59, 4717.
18. (a) Suzuki, A. Acc. Chem. Res. 1982, 15, 178.
19. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
20. (c) Suzuki, A. J. Organomet. Chem. 1998, 576, 147.
21. (d) Darses, S.; Genet, J. P. Eur. J. Org. Chem. 2003, 4313.
22. Sakai, M.; Euda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279.
23. (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics. 1997, 16, 4229.
24. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479.
25. (a) Duan, H. F.; Xie, J. H.; Shi, W. J.; Zhang, Q.; Zhou, Q. L. Org. Lett. 2006, 8, 1479.
26. (b) Son, S. U.; Kim, S. B.; Reingold, J. A.; Carpenter, G. B.; Sweigart, D. A. J. Am. Chem. Soc. 2005,127, 12238.
27. (c) Pucheault, M.; Darses, S.; Genet, J. P. Chem. Commun. 2005, 4714.
28. (d) Focken, T.; Rudolph, J.; Bolm, C. Synthesis 2005, 3, 429.
29. (e) Jagt, R. B. C.; Toullec, P. Y.; Vries, J. G. D.; Feringa, B. L.; Minnaard, A. J. Org. Biomol. Chem. 2006, 4, 773.
30. (f) Suzuki,K.; Kondo, K.; Aoyama, T. Synthesis 2006, 1360.
31. (j) Gois, P. M. P.; Trindade, A. F.; Veiros, L. F.; Andre, V.; Duarte, M. T.; Afonso, C. A. M.; Caddick, S.; Cloke, F. G. N. Angew. Chem., Int. Ed. 2007, 46, 5750.
32. (h) Gois, P. M. P.; Trindade, A. F.; Veiros, L. F.; Andre, V.; Duarte, M. T.; Afonso, C. A. M.; Caddick, S.; Cloke, F. G. N. J. Org. Chem. 2008, 73, 4076.
33. (a) Gibson, S.; Foster, D. F.; Eastham, G. R.; Tooze, R. P.; Cole, H. D. J. Chem. Commun. 2001, 779.
34. (b) Yamamoto, T.; Ohta, T.; Ito, Y. Org. Lett. 2005, 7, 4153.
35. (c) Suzuki, K.; Arao, T.; Ishii, S.; Maeda, Y.; Kondo, K.; Aoyama, T. Tetrahedron Lett. 2006, 47, 5789.
36. (d) He, P.; Lu, Y.; Dong, C. G.; Hu, Q. S. Org. Lett. 2007, 9, 343.
37. (e) He, P.; Lu, Y.; Hu, Q. S. Tetrahedron Lett. 2007, 48, 5283.
38. Qin, C. M.; Wu, H. Y.; Cheng, J.; Chen, X. A.; Liu, M. C.; Zhang, W. W.; Su, W. K.; Ding, J. C. J. Org. Chem. 2007, 72, 4102.
39. (a) Tolman, C. A. Chem. Rev. 1977, 77, 313.
40. (b) Braga, A. A. C.; Morgon, N. H.; Ujaque, G.; Liedos, A.; Maseras, F. J. Organomet. Chem. 2006, 691, 4459.
41. (c) Braga, A. A. C.; Morgon, N. H.; Ujaque, G.; Maseras, F. J. Am. Chem. Soc. 2005, 127, 9298.
42. (d) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
43. (e) Kranenburg, M.; vanderBurgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1995, 14, 3081.
44. (f) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.