Insights into the mechanism of the Negishi reaction: ZnRX versus ZnR 2 reagents

Journal of the American Chemical Society

Volumn 129, Issue 12, 2007, Pages 3508-3509

  Casares, Juan A ^a   Espinet, Pablo ^a   Fuentes, Beatriz ^a   Salas, Gorka ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC COMPOUND; REAGENT; ZINC COMPLEX;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERIZATION; NEGISHI REACTION; STEREOCHEMISTRY;

EID: 33947680107     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja070235b     Document Type: Article

References (22)

1. (a) Komiya, S.; Hirano, M. In Fundamentals of Molecular Catalysis; Kurosawa, H., Yamamoto, A., Eds.; Elsevier: Amsterdam, The Netherlands, 2003; Chapter 3.
2. Ozawa, F. In Fundamentals of Molecular Catalysis; Kurosawa, H., Yamamoto, A., Eds.; Elsevier: Amsterdam, The Netherlands, 2003; Chapter 9.
3. (b) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852-860.
4. (a) Espinet, P.; Echavarren, A. Angew. Chem. Int. Ed. 2004, 43, 4704-4734.
5. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959.
6. (a) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; Vol. 1, Part III.
7. (b) Negishi, E.; Zeng, X.; Tan, Z.; Qian, M.; Hu, Q.; Huang, Z. Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 15.
8. (a) Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 12527-12530.
9. (b) Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 14726-14727.
10. (c) Tan, Z.; Negishi, E. Angew. Chem., Int. Ed. 2006, 45, 762-765.
11. (d) Jones, G. D.; Martin, J. L.; McFarland, C.; Allen, O. R.; Hall, R. E.; Haley, A. D.; Bandon, R. J.; Konovalova, T.; Desrochers, P. J.; Pulay, P.; Vicic, D. A. J. Am. Chem. Soc. 2006, 128, 13175-13183.
12. (e) Jones, G. D.; McFarland, C.; Anderson, T. J.; Vicic, D. A. Chem. Commun. 2005, 4211-4213.
13. 19F, as applied in studies on the Stille reaction. See for instance: (a) Casares, J. A.; Espinet, P.; Salas, G. Chem.-Eur. J. 2002, 8, 4843-4853.
14. (b) Casado, A. L.; Espinet, P.; Gallego, A. M.; Martínez-Ilarduya, J. M. Chem. Commun. 2001, 339-340.
15. (c) Casado, A. L.; Espinet, P.; Gallego, A. M. J. Am. Chem. Soc. 2000, 122, 11771-11782.
16. (d) Casado, A. L.; Espinet, P.; Gallego, A. M. J. Am. Chem. Soc. 1998, 120, 8978-8985.
17. 3. For details see Supporting Information.
18. 2 in THF.
19. (a) Mendes, P. Comput. Appl. Biosci. 1993, 9, 563-571.
20. (b) Mendes, P. Trends Biochem. Sci. 1997, 22, 361-363.
21. (c) Mendes, P.; Kell, D. B. Bioinformatics 1998, 14, 869-883.
22. (d) Martins, A. M.; Mendes, P.; Cordeiro, C.; Freire, A. P. Eur. J. Biochem. 2001, 268, 3930-3936.