Suzuki-Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols

Tetrahedron Letters

Volumn 45, Issue 17, 2004, Pages 3511-3515

  Arentsen, Katherine ^a   Caddick, Stephen ^b   Cloke, F Geoffrey N ^a   Herring, Adam P ^c   Hitchcock, Peter B ^a  

^a UNIVERSITY OF SUSSEX   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c ASTRAZENECA   (United Kingdom)

Author keywords

Alkyl bromides; Aryl chlorides; Palladium; Suzuki

Indexed keywords

BORONIC ACID DERIVATIVE; CHLORINE DERIVATIVE; HALIDE; IMIDAZOLE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; SUZUKI REACTION;

LATEOLABRAX JAPONICUS;

EID: 1842738116     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.134     Document Type: Article

References (28)

1. Diederich F., Stang P.J. Metal-Catalyzed Cross-Coupling Reactions. 1998;Wiley-VCH, Weinheim.
2. Tsuji J. Palladium Reagents and Catalysts. 1995;Wiley, Chichester.
3. Stanforth S.P. Tetrahedron. 54:1998;263-303.
4. Collman J.P., Hegedus L.S., Norton J.R., Finke R.G. Principles and Applications of Organotransition Metal Chemistry. 1987;University Science Books, Mill Valley, CA.
5. Reviews: Suzuki A. J. Organomet. Chem. 576:1999;147-168.
6. Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457-2483.
7. Suzuki A. Diederich F., Stang P.J. Metal-Catalyzed Cross-Coupling Reactions. 1998;Wiley-VCH, Weinheim.
8. For a review on aryl chlorides in cross-coupling reactions, see: Littke A.F., Fu G.C. Angew. Chem., Int. Ed. 41:2002;4176-4211.
9. Bedford R.B., Cazin C.S.J. Organometallics. 22:2003;987-999.
10. Littke A.F., Dai C., Fu G.C. J. Am. Chem. Soc. 122:2000;4020-4028.
11. Wolfe J.P., Buchwald S.L. Angew. Chem., Int. Ed. 38:1999;2413-2416.
12. Wolfe J.P., Singer R.A., Yang B.H., Buchwald S.L. J. Am. Chem. Soc. 121:1999;9550-9561.
13. Jafarpour L., Nolan S.P. Adv. Organomet. Chem. 46:2001;181-222.
14. Böhm V.P.W., Gstöttmayr C.W.K., Weskamp T., Herrmann W.A. J. Organomet. Chem. 595:2000;186-190.
15. Zhang C., Huang J., Trudell M.L., Nolan S.P. J. Org. Chem. 64:1999;3804-3805.
16. Fürstner A., Leitner A. Synlett. 2001;290-292.
17. IPr·HCl available from Strem Chemicals, catalog number: 07-0590.
18. Gstöttmayr C.W.K., Böhm V.P.W., Herdtweck E., Grosche M., Herrmann W.A. Angew. Chem., Int. Ed. 41:2002;1363-1365.
19. Grasa G.A., Viciu M.S., Huang J., Zhang C., Trudell M.L., Nolan S.P. Organometallics. 21:2002;2866-2873.
20. Caddick S., Kofie W. Tetrahedron Lett. 43:2002;9347-9350.
21. Arnold P.L., Cloke F.G.N., Geldbach T., Hitchcock P.B. Organometallics. 18:1999;3228-3233.
22. Cárdenas D.J. Angew. Chem., Int. Ed. 42:2003;384-387.
23. Netherton M.R., Dai C., Neuschütz K., Fu G.C. J. Am. Chem. Soc. 123:2001;10099-10100.
24. Kirchhoff J.H., Dai C., Fu G.C. Angew. Chem., Int. Ed. 41:2002;1945-1947.
25. Netherton M.R., Fu G.C. Angew. Chem., Int. Ed. 41:2002;3910-3912.
26. Kirchhoff J.H., Netherton M.R., Hills I.D., Fu G.C. J. Am. Chem. Soc. 124:2002;13662-13663.
27. Eckhardt M., Fu G.C. J. Am. Chem. Soc. 125:2003;13642-13643.
28. For the use of TBAB in Pd free Suzuki reactions, see: Leadbeater N.E., Marco M. Angew. Chem., Int. Ed. 42:2003;1407-1409.