Amination of aryl chlorides in water catalyzed by cyclopalladated ferrocenylimine complexes with commercially available monophosphinobiaryl ligands

Tetrahedron Letters

Volumn 48, Issue 9, 2007, Pages 1619-1623

  Xu, Chen ^a   Gong, Jun Fang ^a   Wu, Yang Jie ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

Amination; Aryl chloride; Cyclopalladated ferrocenylimine complex; Monophosphinobiaryl ligand; Water

Indexed keywords

AMINE; CHLORIDE; FERROCENE DERIVATIVE; LIGAND; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM HYDROXIDE; TERT BUTYL ALCOHOL;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION;

EID: 33846702580     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.130     Document Type: Article

References (30)

1. For reviews see:. Schlummer B., and Scholz U. Adv. Synth. Catal. 346 (2004) 1599 and references cited therein
2. Buchwald S.L., Mauger C., Mignani G., and Scholz U. Adv. Synth. Catal. 348 (2006) 23
3. Hartwig J.F. Synlett 9 (2006) 1283
4. Wolfe J.P., and Buchwald S.L. Angew. Chem., Int. Ed. 38 (1999) 2413
5. Wolfe J.P., Tomori H., Sadighi J.P., Yin J., and Buchwald S.L. J. Org. Chem. 65 (2000) 1158
6. Huang X.H., Anderson K.W., Zim D., Jiang L., Klapars A., and Buchwald S.L. J. Am. Chem. Soc. 125 (2003) 6653
7. Kataoka N., Shelby Q., Stambuli J.P., and Hartwig J.F. J. Org. Chem. 67 (2002) 5553
8. Shen Q., Shekhar S., Stambuli J.P., and Hartwig J.F. Angew. Chem., Int. Ed. 44 (2005) 1371
9. Rataboul F., Zapf A., Jackstell R., Harkal S., Riermeier T., Monsees A., Dingerdissen U., and Beller M. Chem. Eur. J. 10 (2004) 2983
10. Harkal S., Rataboul F., Zapf A., Fuhrmann C., Riermeier T., Monsees A., and Beller M. Adv. Synth. Catal. 346 (2004) 1742
11. Dai Q., Gao W., Liu D., Kapes L.M., and Zhang X. J. Org. Chem. 71 (2006) 3928
12. Xie X., Zhang T., and Zhang Z. J. Org. Chem. 71 (2006) 6522
13. Hill L.L., Moore L.R., Huang R., Craciun R., Vincent A.J., Dixon D.A., Chou J., Woltermann C.J., and Shaughnessy K.H. J. Org. Chem. 71 (2006) 5117
14. Urgaonkar S., and Verkade J.G. J. Org. Chem. 69 (2004) 9135 and references cited therein
15. Huang J., Grasa G., and Nolan S.P. Org. Lett. 1 (1999) 1307
16. Grasa G.A., Viciu M.S., Huang J., and Nolan S.P. J. Org. Chem. 66 (2001) 7729
17. Marion N., Navarro O., Mei J., Stevens E.D., Scott N.M., and Nolan S.P. J. Am. Chem. Soc. 128 (2006) 4101 and references cited therein
18. For palladacyclic precatalysts in amination of aryl chlorides see:. Schnyder A., Indolese A.F., Studer M.H., and Blaser U. Angew. Chem., Int. Ed. 41 (2002) 3668
19. Viciu M.S., Kelly III R.A., Stevens E.D., Naud F., Studer M., and Nolan S.P. Org. Lett. 5 (2003) 1479
20. Bedford R.B., Cazin C., Coles S.J., Gelbrich T.P., Horton N., Hursthouse M.B., and Light M.E. Organometallics 22 (2003) 987
21. Bedford R.B., and Blake M.E. Adv. Synth. Catal. 345 (2003) 1107
22. Zim D., and Buchwald S.L. Org. Lett. 5 (2003) 2413
23. Grieco P.A. Organic Synthesis in Water (1998), Blackie Academic & Professional, New York
24. Li C.J., and Chan T.H. Organic Reaction in Aqueous Media (1998), Wiley & Sons, New York
25. Kuwano R., Utsunomiya M., and Hartwig J.F. J. Org. Chem. 67 (2002) 6479
26. Yin J., Zhao M.M., Huffman M.A., and McNamara J.M. Org. Lett. 4 (2002) 3481
27. Gooßen L.J., Paetzold J., Briel O., Rivas-Nass A., Karch R., and Kayser B. Synlett 2 (2005) 275
28. Gong J.F., Liu G.Y., Du C.X., Zhu Y., and Wu Y.J. J. Organomet. Chem. 690 (2005) 3963
29. Xu C., Gong J.F., Yue S.F., Zhu Y., and Wu Y.J. Dalton Trans. (2006) 4730
30. 1H NMR.