An efficient and mild ortho-zincation of aromatics and heterocycles by using TMP2Mg·2LiCl in the presence of ZnCl2

Journal of Organometallic Chemistry

Volumn 695, Issue 5, 2010, Pages 775-780

  Dong, Zhi Bing ^a   Zhu, Wei Hua ^a   Zhang, Zhi Guang ^b   Li, Min Zhi ^a  

^a JIANGSU UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

Aromatics; Functionalization; Heterocycles; Metalation; Zincation

Indexed keywords

ELECTROPHILES; FUNCTIONALIZATIONS; FUNCTIONALIZED; GOOD YIELD; HETEROCYCLES; METALATIONS; ZINC REAGENTS; ZINCATION;

ZINC;

THERMOMECHANICAL PULPING PROCESS;

EID: 75749114101     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2009.12.016     Document Type: Article

References (30)

1. Schlosser M. Angew. Chem., Int. Ed. 44 (2005) 376
2. Heiss C., Marzi E., Mongin F., and Schlosser M. Eur. J. Org. Chem. (2007) 669
3. Schlosser M. Eur. J. Org. Chem. (2001) 3975
4. Hodgson D.M., Bray C.D., and Kindon N.D. Org. Lett. 7 (2005) 2305
5. Yus M., and Foubelo F. In: Knochel P. (Ed). Handbook of Functionalized Organometallics vol. 1 (2005), Wiley-VCH, Weinheim 7
6. Snieckus V. Chem. Rev. 90 (1990) 879
7. Clayden J., Stimson C.C., and Keenan M. Chem. Commun. (2006) 1393
8. Eaton P.E., Lee C.H., and Xiong Y. J. Am. Chem. Soc. 111 (1989) 8016
9. Eaton P.E., and Lukin K.A. J. Am. Chem. Soc. 115 (1993) 11370
10. Beak P., and Snieckus V. Angew. Chem., Int. Ed. 43 (2004) 2206
11. Seggio A., Chevallier F., Vaultier M., and Mongin F. J. Org. Chem. 72 (2007) 6602
12. Plé N., Turck A., Couture K., and Queguiner G. J. Org. Chem. 60 (1995) 3781
13. Chevallier F., and Mongin F. Chem. Soc. Rev. 37 (2008) 595
14. Mongin F., and Quéguiner G. Tetrahedron 57 (2001) 4059
15. Turck A., Plé N., Mongin F., and Quéguiner G. Tetrahedron 57 (2001) 4489
16. Quéguiner G. J. Heterocycl. Chem. 37 (2000) 615
17. Clososki G.C., Rohbogner C.J., and Knochel P. Angew. Chem., Int. Ed. 46 (2007) 7681
18. Rohbogner C.J., Clososki G.C., and Knochel P. Angew. Chem., Int. Ed. 47 (2008) 1503
19. Dong Z.B., Clososki G.C., Wunderlich S.H., Unsinn A., Li J.S., and Knochel P. Chem. Eur. J. 15 (2009) 457
20. Knochel P., Yeh M.C.P., Berk S.C., and Talbert J. J. Org. Chem. 53 (1988) 2390
21. Negishi E., Valente L.F., and Kobayashi M. J. Am. Chem. Soc. 102 (1980) 3298
22. Negishi E., and Kobayashi M. J. Org. Chem. 45 (1980) 5223
23. Negishi E. Acc. Chem. Res. 15 (1982) 340
24. Milne J.E., and Buchwald S.L. J. Am. Chem. Soc. 126 (2004) 13028
25. Krasovskiy A., Krasovskaya V., and Knochel P. Angew. Chem. 118 (2006) 3024
26. Krasovskiy A., Krasovskaya V., and Knochel P. Angew. Chem., Int. Ed. 45 (2006) 2958
27. P. Knochel, V. Krasovskaya, A. Krasovkiy, Eur. Pat. Appl. EP 1810974 A1, 2007.
28. Hammett L.P., Walden G.H., and Edmonds S.M. J. Am. Chem. Soc. 56 (1934) 1092
29. Epifani E., Florio S., Ingrosso G., Sgarra R., and Stasi F. Tetrahedron 43 (1987) 2769
30. Lin W., Baron O., and Knochel P. Org. Lett. 8 (2006) 5673