CuCl/bipyridine-catalyzed addition reactions of arylboroxines with aldehydes, α,β-unsaturated ketones, and N-tosyl aldimines

Journal of Organic Chemistry

Volumn 76, Issue 18, 2011, Pages 7602-7607

  Liao, Yuan Xi ^a   Hu, Qiao Sheng ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDIMINES; ELEVATED TEMPERATURE; MICROWAVE ENERGIES; N-TOSYL ALDIMINES; UNSATURATED KETONES;

ADDITION REACTIONS; ALDEHYDES; CATALYSIS; KETONES;

ORGANIC COMPOUNDS;

ALDEHYDE DERIVATIVE; BIPYRIDINE; BORON DERIVATIVE; COPPER CHLORIDE; IMINE; KETONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; ENERGY; HIGH TEMPERATURE; MICROWAVE IRRADIATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 80052714121     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201338v     Document Type: Article

References (50)

1. Partyka, D. V. Chem. Rev. 2011, 111, 1529-1595
2. Miyaura, N. Synlett 2009, 2039-2050
3. Gutnov, A. Eur. J. Org. Chem. 2008, 4547-4554
4. Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 3364-3366
5. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829-2844
6. Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169-196 and references cited therein
7. Morikawa, S.; Michigami, K.; Amii, H. Org. Lett. 2010, 12, 2520-2523
8. Trindade, A. F.; Andre, V.; Duarte, M. T.; Veiros, L. F.; Gois, P. M. P.; Afonso, C. A. M. Tetrahedron 2010, 66, 8494-8502
9. Ma, Q.; Ma, Y.; Liu, X.; Duan, W.; Qu, B.; Song, C. Tetrahedron: Asymmetry 2010, 21, 292-298
10. White, J. R.; Price, G. J.; Plucinski, P. K.; Frost, C. G. Tetrahedron Lett. 2009, 50, 7365-7368
11. Kuriyama, M.; Ishiyama, N.; Shimazawa, R.; Onomura, O. Tetrahedron 2010, 66, 6814-6819
12. Zhang, R.; Xu, Q.; Zhang, X.; Zhang, T.; Shi, M. Tetrahedron: Asymmetry 2010, 21, 1928-1935
13. Suzuma, Y.; Hayashi, S.; Yamamoto, T.; Oe, Y.; Ohta, T.; Ito, Y. Tetrahedron: Asymmetry 2009, 20, 2751-2758
14. Bouffard, J.; Itami, K. Org. Lett. 2009, 11, 4410-4413
15. Zhou, L.; Du, X.; He, R.; Ci, Z.; Bao, M. Tetrahedron Lett. 2009, 50, 406-408
16. Sakurai, F.; Kondo, K.; Aoyama, T. Tetrahedron Lett. 2009, 50, 6001-6003
17. Tomita, D.; Kanai, M.; Shibasaki, M. Chem. Asian J. 2006, 1, 161-166
18. Zheng, H.; Zhang, Q.; Chen, J.; Liu, M.; Cheng, S.; Ding, J.; Wu, H.; Su, W. J. Org. Chem. 2009, 74, 943-945
19. Shintani, R.; Takatsu, K.; Hayashi, T. Chem. Commun. 2010, 46, 6822-6824
20. Zou, T.; Pi, S.-S.; Li, J.-H. Org. Lett. 2009, 11, 453-456
21. Yamamoto, Y.; Kurihara, K.; Miyaura, N. Angew. Chem., Int. Ed. 2009, 48, 4414-4416
22. Karthikeyan, J.; Jeganmohan, M.; Cheng, C.-H. Chem.-Eur. J. 2010, 16, 8989-8992
23. Jia, X.; Fang, L.; Lin, A.; Pan, Y.; Zhu, C. Synlett 2009, 495-499
24. Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527-2572
25. Beletskaya, I. P.; Cheprakov, A. V. J. Organomet. Chem. 2004, 689, 4055-4082
26. Bedford, R. B. Chem. Commun. 2003, 1787-1796
27. Newkome, G. R.; Puckett, W. E.; Gupta, V. K.; Kiefer, G. E. Chem. Rev. 1986, 86, 451-489
28. He, P.; Lu, Y.; Dong, C.-G.; Hu, Q.-S. Org. Lett. 2007, 9, 343-346
29. He, P.; Lu, Y.; Hu, Q.-S. Tetrahedron Lett. 2007, 48, 5283-5288
30. Liao, Y.-X; Xing, C.-H.; He, P.; Hu, Q.-S. Org. Lett. 2008, 10, 2509-2512
31. Liao, Y.-X; Xing, C.-H.; Israel, M.; Hu, Q.-S. Tetrahedron. Lett. 2011, 52, 3324-3328
32. Liao, Y.-X.; Xing, C.-H.; Israel, M.; Hu, Q.-S. Org. Lett. 2011, 52, 3324-3328
33. Yu, A.; Cheng, B.; Wu, Y.; Li, J.; Wei, K. Tetrahedron Lett. 2008, 49, 5405-5407
34. Bedford, R. B.; Betham, M.; Charmant, J. P. H.; Haddow, M. F. A.; Orpen, G.; Pilarski, L. T.; Coles, S. J.; Hursthouse, M. B. Organometallics 2007, 26, 6346-6353
35. Xing, C.-H.; Hu, Q.-S. Tetrahedron Lett. 2010, 51, 924-927
36. Xing, C.-H.; Liu, T.-P.; Zheng, J. R.; Ng, J.; Eposito, M.; Hu, Q.-S. Tetrahedron Lett. 2009, 50, 4953-4957
37. Xing, C.-H; Liao, Y.-X.; He, P.; Hu, Q.-S. Chem. Commun. 2010, 46, 3010-3012
38. Li, Q.; Dong, Z.; Yu, Z.-X. Org. Lett. 2011, 13, 1122-1125
39. Nishimura, T.; Yasuhara, Y.; Sawano, T.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 7872-7873
40. Wang, Y.-Z.; Hu, X.-C.; Du, H.-F. Org. Lett. 2010, 12, 5482-5485
41. Drinkel, E.; Briceno, A.; Dorta, R.; Dorta, R. Organometallics 2010, 29, 2503-2514
42. Chen, J.; Chen, J.-M.; Lang, F.; Zhang, X.-Y.; Cun, L.-F.; Zhu, J.; Deng, J.-G.; Liao, J. J. Am. Chem. Soc. 2010, 132, 4552-4553
43. Hahn, B. T.; Tewes, F; Froehlich, R.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 1143-1146
44. Lin, S.; Lu, X. Org. Lett. 2010, 12, 2536-2539
45. For a report on Cu-catalyzed addition reaction of organoborons with α,β-unsaturated esters, see: Ohmiya, H.; Yoshida, M.; Sawamura, M. Org. Lett. 2011, 13, 482-485
46. Luo, Y.; Carnell, A. J. Angew. Chem., Int. Ed. 2010, 49, 2750-2754
47. Brak, K.; Ellman, J. A. J. Org. Chem. 2010, 75, 3147-3150
48. Dai, H.; Lu, X. Tetrahedron Lett. 2009, 50, 3478-3481
49. Wang, Z.-Q; Feng, C.-G; Xu, M.-H.; Lin, G.-Q. J. Am. Chem. Soc. 2007, 129, 5336-5337
50. Pucheault, M.; Darses, S.; Genet, J.-P. Chem. Commun. 2005, 37, 4714-4716