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(a) Okuro, K.; Furuune, M.; Enna, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 4716-4721 and references therein.
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See also ref 2a
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(b) See also ref 2a.
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8
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33751554191
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(c) A discussion on possible roles of Cu(I) in Pd/Cu catalytic systems: Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359-5364.
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0037442583
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(a) Mori et al. have recently reported the use of fluoride salts in the Pd/Cu-catalyzed arylation of thiazole. Selective phenylation of 2-position was achieved at mild temperatures. Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.; Osakada, K.; Kawamoto, M.; Ikeda, T. J. Am. Chem. Soc. 2003, 125, 1700-1701.
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13
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0142100404
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note
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1,3-Bis-mesitylimidazolium chloride is commercially available from Strem. It can also be prepared according to the procedure described in Arduengo, A. J., III (E. I. Du Pont de Nemours & Company), US 5.077.414 A2, 1992; WO 91/14678.
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14
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0142100405
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note
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In a typical procedure, anhydrous cobalt(II) acetate and the ligand were stirred at room temperature to form the active catalyst system, prior to the addition of the other reagents. This sequence of addition of ingredients proved to be important for the success of the method. For more detailed experimental procedures, see the Supporting Information.
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15
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0142068781
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note
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These prices are quoted from the Aldrich Catalog, Aldrich, Milwaukee, WI, 2003.
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16
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0029955627
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The indirect methods require lithiation and transmetalation to zinc (to prevent oxazole ring cleavage) prior to cross-coupling. Anderson, B. A.; Harn, N. K. Synthesis 1996, 583-585.
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Anderson, B.A.1
Harn, N.K.2
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17
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0142132069
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note
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The mechanistic picture for the palladium-catalyzed arylation of heteroarenes has not been elucidated either. For discussion and references on this topic, see ref 3.
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18
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37049074849
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Bhandal, H.; Patel, V. F.; Pattenden, G.; Russell, J. J. J. Chem. Soc., Perkin Trans. 1 1990, 2691-2701.
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(c) Avedissian, H.; Bérillon, L.; Cahiez, G.; Knochel, P. Tetrahedron Lett. 1998, 39, 6163-6166.
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(e) Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 4137-4139. Kneisel, F. F.; Monguchi, Y.; Knapp, K. M.; Zipse, H.; Knochel, P. Tetrahedron Lett. 2002, 43, 4875-4879.
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(e) Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 4137-4139. Kneisel, F. F.; Monguchi, Y.; Knapp, K. M.; Zipse, H.; Knochel, P. Tetrahedron Lett. 2002, 43, 4875-4879.
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Kneisel, F.F.1
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Knochel, P.5
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0142132068
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Ph-Co(III) complexes have been prepared via this route. Lampeka, J. D.; Jäger, E.-G.; Müller, K.; Schade, W. Z. Chem. 1988, 28, 70.
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Grimmett, M.R.1
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29
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0034686883
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The effect of cobalt on the regiochemical course of intramolecular coupling between an aryl bromide and the pyridine ring has been observed. Harrowven, D. C.; Nunn, M. I. T.; Blumire, N. J.; Fenwick, D. R. Tetrahedron Lett. 2000, 41, 6681-6683.
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Fenwick, D.R.4
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0037012428
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A metal-carbene intermediate should also be considered. For interesting reading on related topics, see: (a) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 3202-3203. (b) Gründemann, S.; Kovacevic, A.; Albrecht, M.; Faller, J. W.; Crabtree, R. H. J. Am. Chem. Soc. 2002, 124, 10473-10481.
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Tan, K.L.1
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Ellman, J.A.3
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31
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0037019663
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A metal-carbene intermediate should also be considered. For interesting reading on related topics, see: (a) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 3202-3203. (b) Gründemann, S.; Kovacevic, A.; Albrecht, M.; Faller, J. W.; Crabtree, R. H. J. Am. Chem. Soc. 2002, 124, 10473-10481.
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Crabtree, R.H.5
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