Palladium-catalysed alkynylation of 2- or 3-bromopyridine

(a) Sonogashira K. , Tohda Y. , and Hagihara N. , Tetrahedron Lett., 1975, 16, 4467; (b) L. Cassar, J. Organomet. Chem., 1975, 93, 253; (c) H.A Dieck and F.R. Heck, J. Organomet. Chem., 1975, 93, 259.

For reviews, see: (a) Sonogashira K. In Comprehensive Organic Synthesis, Trost B.M , and Fleming I. , (eds.) Pergamon Press, New York, 1991, vol. 3, 521; (b) R. Rossi, A. Carpita and F. Bellina, Org. Prep. Proc. Int., 1995, 27, 129; (c) J. Tsuji, Palladium Reagents and Catalysts. Wiley, Chichester, 1995, p. 168; (d) K.C. Nicolaou and E.J. Sorensen, Classics in Total Synthesis. VCH, Weinheim, 1996, p. 582; (e) L. Brandsma, S.F. Vasilevsky and H.D. Verkruijsse, Application of Transition Metal Catalysts in Organic Synthesis, Springer, Berlin, 1998, p. 179; (f) K. Sonogashira In Metal-Catalysed Cross-Coupling Reactions, F. Diederich and P.J. Stang, (eds.) Wiley-VCH, Weinheim, 1998, p. 203.

For examples using aryl bromides in the Sonogashira reaction, see: (a) Lemhadri M. , Doucet H. , and Santelli M. , Synthesis, 2005, 1359; (b) M. Lopez-Deber, L. Castedo and J. Granja, Org. Lett., 2001, 3, 2823; (c) M. Unroe and B. Reinhardt, Synthesis, 1987, 981; (d) L. Bleicher N. Cosford A. Herbaut, J. McCallum and I. McDonald, J. Org. Chem., 1998, 63, 1109; (e) M. Inouye, K. Fujimoto M. Furusyo and H. Nakazumi, J. Am. Chem. Soc., 1999, 121, 1452; (f) A. Basak, J. Shain, K. Khamrai, K Rudra and A. Basak, J. Chem. Soc., Perkin Trans. 1, 2000, 1955.

Siemsen P. , Livingston R.C. , and Diederich F. , Angew. Chem. Int. Ed., 2000, 39, 2632.

(a) Cheng J. , Wang F. , Xu J. , Pan Y. , and Zhang Z. , Tetrahedron Lett., 2003, 44, 7095; (b) J. Cheng, Y. Sun, F. Wang, J. Xu, Y. Pan and Z. Zhang, J. Org. Chem, 2004, 69, 5428.

Mukaiyama T. , Kikuchi W. , and Shintou T. , Chem. Lett., 2003, 32, 300.

Lemhadri M. , Doucet H. , and Santelli M. , Synthesis, 2005, 1359.

Novak Z. , Szabo A. , Repasi J. , and Kotschy A , J. Org. Chem., 2003, 68, 3327.

Erdelyi M. , and Gogoll A. , J. Org. Chem, 2001, 66, 4165.

Nagy T. , Csampai A. , and Kotschy A. , Tetrahedron, 2005, 61, 9767.

Li P. , Wang L. , and Li H. , Tetrahedron, 2005, 61, 8633.