In the presence of triphenylphosphine, a novel Cu(II)-catalysed Sonogashira reaction of aryl iodides and bromides with terminal alkynes has been developed, which generates the corresponding cross-coupling products in good yields.
(a) SonogashiraK., TohdaY., and HagiharaN., Tetrahedron Lett.1975, 16, 4467; For selected reviews on Sonogashira reaction, see: (b) K. Sonogashira, In Comprehensive Organic Synthesis, B.M. Trost and I. Fleming, Eds.; Pergamon Press: Oxford, 1991, Vol. 3, Chapter 2.4, pp 521-549; (c) K. Sonogashira, In Metal-Catalysed Cross-Coupling Reactions, F. Diederich and P.J. Stang, Eds.; Wiley-VCH: Weinheim, 1998, pp 203-229; (d) K. Sonogashira, In Handbook of Organopalladium Chemistry for Organic Synthesis, E. Negishi and A. Meijere, Eds.; Wiley-VCH: New York, 2002.
2.
(a) PatersonI., DaviesR.D.M., and MarquezR., Angew. Chem. Int. Ed.2001, 40, 603; (b) M. Toyota, C. Komori and M. Ihara, J. Org. Chem. 2000, 65, 7110; (c) K.C. Nicolaou and W.-M. Dai, Angew. Chem. Int. Ed. 1991, 30, 1387.
3.
(a) CosfordN.D.P., TehraniL., RoppeJ., SchweigerE., SmithN.D., AndersonJ., BristowL., BrodkinJ., JiangX., McDonaldI., RaoS., WashburnM., and VarneyM.A., J. Med. Chem.2003, 46, 204; (b) M. Kort, V. Correa, A.R.P.M. Valentijin, G.A. Marel, B.V.L. Potter, C.W. Taylor and J.H. Boom, J. Med. Chem. 2000, 43, 3295.
4.
(a) NalwaH.S., and MiyataS., Nonlinear Optics of Organic Molecules and Polymers, CRC Press, Boca Raton, FL, 1997; (b) O. Mongin, L. Porres, L. Moreaux, J. Merta and M. Blanchard-Desce, Org. Lett. 2002, 4, 719; (c) L. Brunsveld, E.W. Meijer, R.B. Prince and J.S. Moore, J. Am. Chem. Soc. 2001, 123, 7978.
5.
(a) WegnerG., and MüllenK., Electronic Materials–the Oligomer Approach, Wiley-VCH, Weinheim, 1998; (b) J. Li, A. Ambroise, S.I. Yang, J.R. Diers, J. Seth, C.R. Wack, D.F. Bocian, D. Holten and J.S. Lindsey, J. Am. Chem. Soc., 1999, 121, 8927; (c) R.W. Wagner, J. Seth, S.I. Yang, D. Kim, D.F. Bocian, D. Holten and J.S. Lindsey, J. Org. Chem., 1998, 63, 5042.
6.
(a) HögerS., RosselliS., RammingerA.-D., and EnkelmannV., Org. Lett., 2002, 4, 4269; (b) C.-J. Li, W.T. Slaven IV, V.T. John and S. Banerjee, Chem. Commun., 1997, 1569.
7.
(a) TobeY., UtsumiN., NaganoA., and NaemuraK., Angew. Chem. Int. Ed., 1998, 37, 1285; (b) K. Onitsuka, M. Fujimoto, N. Ohshiro and S. Takahashi, Angew. Chem. Int. Ed., 1999, 38, 689.
8.
(a) HayA.S., J. Org. Chem., 1962, 27, 3320; (b) For a review of acetylenic coupling, see: P. Siemsen, R.C. Livingston and F. Diederich, Angew. Chem., Int. Ed., 2000, 39, 2632.
9.
(a) ZienerU., and GodtA., J. Org. Chem., 1997, 62, 6137; (b) H. Kukula, S. Veit and A. Godt, Eur. J. Org. Chem., 1999, 277.
10.
(a) LeadbeaterN.E., and TominackB.J., Tetrahedron Lett., 2003, 44, 8653; (b) A. Soheili, J. Albaneze-Walker, J.A. Murry, P.G. Dormer and D.L. Hughes, Org. Lett., 2003, 5, 4191; (c) K. Heuzé, D. Méry, D. Gauss and D. Astruc, Chem. Commun., 2003, 2274; (d) L. Djakovitch and P. Rollet, Tetrahedron Lett., 2004, 45, 1367.
11.
(a) ChengJ., SunY., WangF., GuoM., XuJ.-H., PanY., and ZhangZ., J. Org. Chem., 2004, 69, 5428; (b) A. Mori, J. Kawashima, T. Shimada, M. Suguro, K. Hirabayashi and Y. Nishihara, Org. Lett., 2000, 2, 2935; (c) D. Gelman and S.L. Buchwald, Angew. Chem. Int. Ed., 2003, 42, 5993.
12.
ChoudaryB.M., MadhiS., ChowdariN.S., KantamM.L., and SreedharB., J. Am. Chem. Soc., 2002, 124, 14127.
13.
KabalkaG.W., WangL., NamboodiriV., and PagniR.M., Tetrahedron Lett., 2000, 41, 5151.
14.
(a) BeletskayaI.P., LatyshevG.V., TsvetkovA.V., and LukashevN.V., Tetrahedron Lett., 2003, 44, 5011; (b) L. Wang, P. Li and Y. Zhang, Chem. Commun., 2004, 514.
15.
(a) BongD.T., and GhadiriM.R., Org. Lett., 2001, 3, 2509; (b) A.L. Casalnuovo and J.C. Caladrese, J. Am. Chem. Soc., 1990, 112, 4324; (c) H. Dibowski and F.P. Schmidtchen, Tetrahedron Lett., 1998, 39, 525.
16.
ParkS.B., and AlperH., Chem. Commun., 2004, 1306.
17.
(a) ElangovanA., WangY.-H., and HoT-I., Org. Lett., 2003, 5, 1841; (b) H.-F. Chow, C.-W. Wan, K.-H. Low and Y.-Y. Yeung, J. Org. Chem., 2001, 66, 1910; (c) S. Thorand and N. Krause, J. Org. Chem., 1998, 61, 8551.
18.
LeadbeaterN.E., MarcoM., and TominackB.J., Org. Lett., 2003, 5, 3919.
19.
(a) UrgaonkarS., and VerkadeJ.G., J. Org. Chem., 2004, 69, 5752; (b) G. Zhang, Synlett, 2005, 619; (c) P. Li, L. Wang and H. Li, Tetrahedron, 2005, 61, 8633.
20.
MaD., and LiuF., Chem. Commun., 2004, 1934.
21.
HugginsJ.M., and BergmanR.G., J. Am. Chem. Soc., 1981, 103, 3002.
22.
CarpinoL.A., and ChenH.-W., J. Am. Chem. Soc., 1979, 101, 390.
23.
SatoH., IsonoN., MiyoshiI., and MoriM., Tetrahedron, 1996, 52, 8143.
24.
HunterD.H., and CramD.J., J. Am. Chem. Soc., 1966, 88, 5765.
25.
ArcadiA., CacchiS., FabriziG., MarinelliF., and PaceP., Eur. J. Org. Chem., 1999, 12, 3305.
26.
AgawaT., and MillerS.I., J. Am. Chem. Soc., 1961, 83, 449.
27.
YoshidaK., and FuenoT., J. Org. Chem., 1973, 38, 1045.
28.
VasilevA.V., and RudenkoA.P., Russ. J. Org. Chem., 1997, 33, 1555.
