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For representative examples of very efficient catalysts in palladium-catalyzed C-N bond forming reactions, see: a) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723;
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d) J. P. Stambuli, R. Kuwano, J. F. Hartwig, Angew. Chem. 2002, 114, 4940-4942; Angew. Chem. Int. Ed. 2002, 41, 4746-4748;
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e) X. Huang, K. W. Anderson, D. Zim, L. Jiang, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 6653-6655.
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a) A. Y. Lebedev, V. V. Izmer, D. N. Kazyul'kin, I. P. Beletskaya, A. Z. Voskoboynikov, Org. Lett. 2002, 4, 623-626;
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b) J. Barluenga, F. Aznar, M. A. Fernández, C. Valdés, Chem. Commun. 2002, 2362-2363.
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J. P. Wolfe, J. Åhman, J. P. Sadighi, R. A. Singer, S. L. Buchwald, Tetrahedron Lett. 1997, 38, 6367-6370.
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Wolfe, J.P.1
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For other ammonia surrogates in Pd-catalyzed aminations, see: reference [4a] and also: a) K. Hori, M. Mori, J. Am. Chem. Soc. 1998, 120, 7651-7652;
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f) M. C. Harris, X. Huang, S. L. Buchwald, Org. Lett. 2002, 4, 2885.
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a) L. M. Alcazar-Roman, J. F. Hartwig, A. L. Rheingold, L. M. Liable-Sands, I. A. Guzei, J. Am. Chem. Soc. 2000, 122, 4618-4630;
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b) U. K. Singh, E. R. Strieter, D. G. Blackmond, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 14104-14114.
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0003397781
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(Eds: F. Diederich, P. J. Stang), Wiley-VCH, New York, chap. 10
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The palladium-catalyzed C-C bond formation involving organosilanes (Hiyama coupling) is a well-known reaction: T. Hiyama in Metal-catalyzed Cross-coupling Reactions (Eds: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998, chap. 10; however, to the best of our knowledge, the analogous C-N bond-forming reaction has not been described previously.
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Metal-catalyzed Cross-coupling Reactions
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Hiyama, T.1
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0023915664
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E. W. Colvin, D. McGarry, M. J. Nugent, Tetrahedron 1988, 44, 4157-4172.
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25
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0348183377
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note
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Reactions carried out in the presence of CsF in dioxane as solvent gave rise to the cross-coupling product together with considerable amounts of decomposition materials derived from the imine.
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26
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0348183376
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note
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These results indicate that strong nucleophiles tend to promote the N-Si bond cleavage at a much faster rate than the catalytic process itself, giving rise to decomposition of the imine instead of coupling-product formation.
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27
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0032560932
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D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722.
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J. Am. Chem. Soc.
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Old, D.W.1
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Buchwald, S.L.3
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28
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0029743317
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The inhibition of the β-elimination pathway was a major challenge in the early work of palladium-catalyzed aryl amination. In fact, catalysts based on chelating ligands such as binap and dppf, so-called second-generation catalysts, favor reductive elimination, thus lowering the amount of β-elimination products: a) J. P. Wolfe, S. Wagaw, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 7215-7216;
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Wolfe, J.P.1
Wagaw, S.2
Buchwald, S.L.3
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0034249672
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see also: c) P. W. N. M. van Leeuwen, P. C. J. Kamer, J. N. H. Reek, P. Dierkes, Chem. Rev. 2000, 100, 2741-2769.
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Van Leeuwen, P.W.N.M.1
Kamer, P.C.J.2
Reek, J.N.H.3
Dierkes, P.4
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31
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0141519681
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The β-elimination pathway in the presence of a Pd catalyst based on 4b was recently adapted into a new method for the oxidation of alcohols: A. S. Guram, X. Bei, H. W. Turner, Org. Lett. 2003, 5, 2485-2487.
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Guram, A.S.1
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Turner, H.W.3
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32
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0037074333
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a) For a review of the synthetic applications of azadienes, see: S. Jayakumar, M. P. S. Ishar, M. P. Mahajan, Tetrahedron 2002, 58, 379-471;
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Jayakumar, S.1
Ishar, M.P.S.2
Mahajan, M.P.3
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33
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0037155508
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see also: b) F. Palacios, C. Alonso, P. Amezua, G. Rubiales, J. Org. Chem. 2002, 67, 1941-1946.
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Palacios, F.1
Alonso, C.2
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0000518455
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G. Cainelli, D. Giacomini, P. Galletti, A. Gaiba, Synlett, 1996, 657.
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Cainelli, G.1
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