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

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

References

• 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