RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2007(7): 1061-1069
DOI: 10.1055/s-2007-965952
DOI: 10.1055/s-2007-965952
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Substituted 2,2′-Bipyridines from 2-Bromo- or 2-Chloropyridines Using Tetrakis(triphenylphosphine)palladium(0) as a Catalyst in a Modified Negishi Cross-Coupling Reaction
Weitere Informationen
Received
4 January 2007
Publikationsdatum:
28. Februar 2007 (online)
Publikationsverlauf
Publikationsdatum:
28. Februar 2007 (online)
![](https://www.thieme-connect.de/media/synthesis/200707/lookinside/thumbnails/10.1055-s-2007-965952-1.jpg)
Abstract
A protocol for an efficient, modified Negishi cross-coupling strategy for substituted 2,2′-bipyridines employing tetrakis(triphenylphosphine)palladium(0) as a simple, commercially available, and relatively inexpensive catalyst for both 2-bromo- and 2-chloropyridines has been developed. Further transformations were carried out yielding some new valuable functionalized 2,2′-bipyridines.
Key words
Negishi reaction - 2,2′-bipyridines - cross-coupling reactions - organozinc compounds - palladium
-
1a
Kaes C.Katz A.Hosseini MW. Chem. Rev. 2000, 100: 3553 -
1b
Newkome GR.Patri AK.Holder E.Schubert US. Eur. J. Org. Chem. 2002, 235 - 2
Piguet C.Bernadinelli G.Hopfgartner G. Chem. Rev. 1997, 97: 2005 - 3
Juris A.Balzani V.Barigelletti F.Campagna S.Belser P.von Zelewsky A. Coord. Chem. Rev. 1998, 84: 85 -
4a
Chelucci G.Thummel RP. Chem. Rev. 2002, 102: 3129 -
4b
Fletcher NC. J. Chem. Soc., Perkin Trans. 1 2002, 1831 - 5
Hassan J.Sévignon M.Gozzi C.Schulz E.Lemaire M. Chem. Rev. 2002, 102: 1359 - 6
Kröhnke F. Synthesis 1976, 1 - Some examples, see:
-
7a
Romero F.Ziessel R. Tetrahedron Lett. 1995, 36: 6471 -
7b
Newkome GR.Gross J.Patri AK. J. Org. Chem. 1997, 62: 3013 -
8a
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
8b
Metal-Catalyzed Cross-Coupling Reactions
2nd ed.:
de Meijere A.Diederich F. Wiley-VCH; Weinheim: 2004. -
8c
Cross-Coupling Reactions
Miyaura N. Springer; Berlin: 2002. - Recent special issue on cross-coupling reactions, see:
- 8d J. Organomet. Chem. 2002, 653: 1-303
- 9
Tsuji J. Palladium Reagents and Catalysts John Wiley & Sons; Chichester: 1995. -
10a
Dai C.Fu GC. J. Am. Chem. Soc. 2001, 123: 2719 -
10b
Littke AF.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 ; Angew. Chem., 2002, 114, 4350 -
11a
Lützen A.Hapke M.Griep-Raming J.Haase D.Saak W. Angew. Chem. Int. Ed. 2002, 41: 2086 ; Angew. Chem., 2002, 114, 2190 -
11b
Schalley CA.Lützen A.Albrecht M. Chem. Eur. J. 2004, 10: 1072 -
12a
Lützen A.Hapke M. Eur. J. Org. Chem. 2002, 2292 -
12b
Lützen A.Hapke M.Staats H.Bunzen J. Eur. J. Org. Chem. 2003, 3948 - 13
Littke AF.Dai C.Fu GC. J. Am. Chem. Soc. 2000, 122: 4020 - 14
Fang Y.-Q.Hanan GS. Synlett 2003, 852 - 15
Grushin V.Alper H. Chem. Rev. 1994, 94: 1047 - 16
Suffert J. J. Org. Chem. 1989, 54: 509 - 17
Leeson PD.Emmett JC. J. Chem. Soc., Perkin Trans. 1 1988, 3085 - 18
Grave C.Lentz D.Schaefer A.Samori P.Rabe JP.Franke P.Schlueter AD. J. Am. Chem. Soc. 2003, 125: 6907 - 19
Baxter PNW. J. Org. Chem. 2000, 65: 1257 - 20
Potts KT. J. Org. Chem. 1985, 50: 5405 - 21
Fletcher NC.Nieuwenhuyzen M.Rainey S. J. Chem. Soc., Dalton Trans. 2001, 2641 - 22 This compound has been described before using a different synthetic approach; however, no NMR or MS data were provided:
Kozhevnikov VN.Kozhevnikov DN.Shabunina OV.Rusinov VL.Chupakhin ON. Tetrahedron Lett. 2005, 46: 1791 - 23
Grosshenny V.Romero FM.Ziessel R. J. Org. Chem. 1997, 62: 1491 - 24 This compound has been described before using a different synthetic approach; however, no NMR or MS data were provided:
Schubert US.Eschbaumer C.Heller M. Org. Lett. 2000, 2: 3373