Cationic Pd(II)/bipyridine-catalyzed addition of arylboronic acids to arylaldehydes. One-pot synthesis of unsymmetrical triarylmethanes

Journal of Organic Chemistry

Volumn 72, Issue 25, 2007, Pages 9757-9760

  Lin, Shaohui ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; CATALYSIS; PALLADIUM; SYNTHESIS (CHEMICAL);

ARYLALDEHYDES; ARYLBORONIC ACIDS; ELECTRON-RICH ARENES; TRIARYLMETHANES;

ORGANIC COMPOUNDS;

ALDEHYDE DERIVATIVE; BIPYRIDINE DERIVATIVE; BORONIC ACID DERIVATIVE; CATION; METHANE; PALLADIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; ELECTRON; METHODOLOGY; ONE POT SYNTHESIS;

2,2'-DIPYRIDYL; ALDEHYDES; BORONIC ACIDS; CATALYSIS; CATIONS; METHANE; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 36849061646     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071232k     Document Type: Article

References (39)

1. (a) de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004.
2. (b) Beller, M.; Bolm, C. Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals; Wiley-VCH: New York, 1998.
3. (a) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
4. (b) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
5. Yamamoto, Y.; Nishikata, T.; Miyaura, N. J. Synth. Org. Chem., Jpn. 2006, 64, 1112.
6. Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2005, 7, 2229.
7. (a) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
8. (b) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Organometallics 2004, 23, 4317.
9. (a) Lu, X. Top. Catal. 2005, 35, 75.
10. (b) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604.
11. (c) Zhang, Q.; Lu, X.; Han, X. J. Org. Chem. 2001, 66, 7676.
12. (d) Zhao, L.; Lu, X. Org. Lett. 2002, 4, 3903.
13. (e) Zhao, L.; Lu, X.; Xu, W. J. Org. Chem. 2005, 70, 4059.
14. (f) Zhao, L.; Lu, X. Angew. Chem., Int. Ed. 2002, 41, 4343.
15. (a) Lu, X.; Lin, S. J. Org. Chem. 2005, 70, 9651.
16. (b) Zhao, B.; Lu, X. Tetrahedron Lett. 2006, 47, 6765.
17. (a) Zhao, B.; Lu, X. Org. Lett. 2006, 8, 5987.
18. (b) Liu, G.; Lu, X. J. Am. Chem. Soc. 2006, 128, 16504.
19. (a) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279.
20. (b) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450.
21. (c) Moreau, C.; Hague, C.; Weller, A. S.; Frost, C. G. Tetrahedron Lett. 2001, 42, 6957.
22. (d) Fuchen, T.; Rudolph, J.; Bolm, C. Synthesis 2005, 429.
23. (e) Duan, H.; Xie, J.; Shi, W.; Zhang, Q.; Zhou, Q. Org. Lett. 2006, 8, 1479.
24. (f) Jagt, R. B. C.; Toullec, P. Y.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Org. Biomol. Chem. 2006, 4, 773.
25. (a) Yamamoto, T.; Ohta, T.; Ito, Y. Org. Lett. 2005, 7, 4153.
26. (b) Suzuki, K.; Arao, T.; Ishii, S.; Maeda, Y.; Kondo, K.; Aoyama, T. Tetrahedron Lett. 2006, 47, 5789.
27. (c) He, P.; Lu, Y.; Dong, C.-G.; Hu, Q.-S. Org. Lett. 2007, 9, 343.
28. (d) During the preparation of this manuscript, we found: Qin, C.; Wu, H.; Cheng, J.; Chen, X.; Liu, M.; Zhang, W.; Su, W.; Ding, J. J. Org. Chem. 2007, 72, 4102.
29. Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Preparations, 2nd ed.; Wiley-VCH: New York, 1999.
30. (a) Muthyala, R.; Katrizky, A. R.; Lan, X. Dyes Pigm. 1994, 25, 303.
31. (b) Shchepinov, M. S.; Korshun, V. A. Chem. Soc. Rev. 2003, 32, 170.
32. (c) Duxbury, D. F. Chem. Rev. 1993, 93, 381.
33. (d) Nair, V.; Abhilash, K. G.; Vidya, N. Org. Lett. 2005, 7, 5857.
34. (e) Esquivias, J.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2006, 45, 629.
35. (f) Ramesh, C.; Banerjee, J.; Pal, R.; Das, B. Adv. Synth. Catal. 2003, 345, 557.
36. (g) Jadav, J. S.; Reddy, B. V. S.; Sunitha, S. Adv. Synth. Catal. 2003, 345, 349.
37. (h) Yadav, J. S.; Reddy, B. V. S.; Murthy, C. V. S. R.; Kumar, G. M.; Madan, C. Synlett 2001, 783.
38. (i) Katritzky, A. R.; Toader, D. J. Org. Chem. 1997, 62, 4137.
39. Strazzolini, P.; Giumanini, A. G.; Verardo, G. Tetrahedron 1994, 50, 217.