Palladium(II)-catalyzed addition of arylboronic acid to nitriles

Tetrahedron Letters

Volumn 47, Issue 38, 2006, Pages 6765-6768

  Zhao, Baowei ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Bipyridine; Ligand; Nitrile; Nucleophilic addition; Palladium

Indexed keywords

ACETOPHENONE; BENZENEBORONIC ACID; BENZOPHENONE; BENZYL CYANIDE DERIVATIVE; BIPYRIDINE; BORONIC ACID DERIVATIVE; NITRILE; PALLADIUM;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; REACTION ANALYSIS;

EID: 33747199035     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.074     Document Type: Article

References (24)

1. For reviews:. Tsuji J. Transition Metal Reagents and Catalysits (2004), Wiley, Chichester
2. Diederich F., and Stang P.J. Metal-Catalyzed Cross-Coupling Reactions (1998), Wiley-VCH, Weinheim
3. de Meijere A., and Diederich F. Metal-Catalyzed Cross-Coupling Reactions. 2nd ed. (2004), John Wiley & Sons, Weinheim, Germany
4. Tamaru Y. In: Negishi E.-i. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 2 (2002), Wiley, New York 1917-1943 and references cited therein
5. Miura M., and Nomura M. Top. Curr. Chem. 219 (2002) 211
6. Hassen J., Sevignon M., Gozzi C., Schulz E., and Lemaire M. Chem. Rev. 102 (2002) 1359
7. Culkin D.A., and Hartiwig J.F. Acc. Chem. Res. 36 (2003) 234
8. Ueura K., Satoh T., and Miura M. Org. Lett. 7 (2005) 2229
9. Kamijo S., Sasaki Y., Kanazawa C., Schüsseler T., and Yamamoto Y. Angew. Chem., Int. Ed. 44 (2005) 7718
10. Larock R.C., Tian Q., and Pletnv A.A.J. J. Am. Chem. Soc. 121 (1999) 3238
11. Pletnv A.A., and Larock R.C. Tetrahedron Lett. 43 (2002) 2133
12. Pletnv A.A., Tian Q., and Larock R.C. J. Org. Chem. 67 (2002) 9276
13. Pletnv A.A., Tian Q., and Larock R.C. J. Org. Chem. 67 (2002) 9428
14. Tian Q., Pletnv A.A., and Larock R.C. J. Org. Chem. 68 (2003) 339
15. Zhou C., and Larock R.C. J. Am. Chem. Soc. 126 (2004) 2302
16. Zhou C., and Larock R.C. J. Org. Chem. 71 (2006) 3551
17. Zhao L., and Lu X. Angew. Chem., Int. Ed. 41 (2002) 4343
18. Lu X., and Lin S. J. Org. Chem. 70 (2005) 9651
19. Suzuki A. Organoboranes in Organic Synthesis (2004), Hokkaido University, Sapporo, Japan
20. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
21. Nakai H., Ogo S., and Watanabe Y. Organometallics 21 (2002) 1674
22. Zhao L., Lu X., and Xu W. J. Org. Chem. 70 (2005) 4069
23. Zhao L., and Lu X. Org. Lett. 4 (2002) 3903
24. 4, and concentrated. The residue was purified by flash chromatography (EtOAc/petroleum ether = 1/50) to give product 1 with 85% yield as a white solid. The detailed characterization data of the products were included in Supplementary data.