Preparation of highly functionalized heterocyclic zinc organometallics via a Li(acac)-catalysis of the I/Zn-exchange reaction

Synlett

Volumn , Issue 2, 2005, Pages 267-270

  Gong, Liu Zhu ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Catalysis; Cross coupling; Diorganozinc reagent; Iodine zinc exchange reaction; Polyfunctional heterocycles

Indexed keywords

ALDEHYDE; COPPER DERIVATIVE; DIORGANOZINC REAGENT; FUNCTIONAL GROUP; HETEROCYCLIC COMPOUND; IODINE; IODINE DERIVATIVE; LITHIUM; LITHIUM CHLORIDE; ORGANIC COMPOUND; ORGANOMETALLIC COMPOUND; REAGENT; UNCLASSIFIED DRUG; ZINC; ZINC DERIVATIVE;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS COUPLING REACTION; EXCHANGE REACTION; NEGISHI CROSS COUPLING REACTION; REACTION ANALYSIS; REPRODUCIBILITY; ROOM TEMPERATURE; SYNTHESIS; TECHNIQUE;

EID: 13844251835     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-837206     Document Type: Article

References (29)

1. Visiting professor from Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences.
2. (a) Gilchrist, T. L. Heterocyclic Chemistry; Longman: Harlow, UK, 1997.
3. (b) Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry; Stanley Thornes: Cheltenham, UK, 1998.
4. (a) Cai, X.; Snieckus, V. Org. Lett. 2004, 6, 2293.
5. (b) Hartung, C. G.; Fecher, A.; Chapell, B.; Snieckus, V. Org. Lett. 2003, 5, 1899.
6. Chauder, B.; Larkin, A.; Snieckus, V. Org. Lett. 2002, 4, 815.
7. Chauder, B.; Green, L.; Snieckus, V. Pure Appl. Chem. 1999, 71, 1521.
8. ( e) Audoux, J.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2004, 60, 6353.
9. (f) Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron 2004, 60, 2181.
10. (g) Dumouchel, S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron 2003, 59, 8629.
11. (h) Quéguiner, G. J. Heterocycl. Chem. 2000, 37, 615.
12. For the preparation of some Grignard reagents with a keto group, see: Kneisel, F. F.; Knochel, P. Synlett 2002, 1799.
13. Kneisel, F. F.; Dochnahl, M.; Knochel, P. Angew. Chem. Int. Ed. 2004, 43, 1017.
14. (a) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
15. (b) Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905.
16. (a) Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298.
17. (b) Kobayashi, M.; Negishi, E. J. Org. Chem. 1980, 45, 5223.
18. Negishi, E. Acc. Chem. Res. 1982, 15, 340.
19. Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Tetrahedron Lett. 1986, 27, 955.
20. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
21. Villieras, J.; Rambaud, M. Synthesis 1982, 924.
22. Sakamoto, T.; Kondo, Y.; Takazawa, N.; Yamanaka, H. J. Chem. Soc., Perkin Trans. 1 1996, 1927.
23. (a) Liu, Y.; Gribble, G. W. Tetrahedron Lett. 2000, 41, 8717.
24. (b) Bergman, J.; Venemalm, L. J. Org. Chem. 1992, 57, 2495.
25. Saulnier, M. G.; Gribble, G. W. J. Org. Chem. 1982, 47, 757.
26. Yang, X.; Althammer, A.; Knochel, P. Org. Lett. 2004, 6, 1665.
27. Collot, V.; Varlet, D.; Rault, S. Tetrahedron Lett. 2000, 41, 4363.
28. Gordon, D. W. Synlett 1998, 1065.
29. 2: 213.0790; found: 213.0795.