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For nickel-catalyzed reactions, see: a) D. Zim, A. L. Monteiro, Tetrahedron Lett. 2002, 43, 4009-4011; b) B. H. Lipshutz, Adv. Synth. Catal. 2001, 343, 313-326; c) B. H. Lipshutz, J. A. Sclafani, P. A. Blomgren, Tetrahedron 2000, 56, 2139-2144; d) S. Saito, S. Oh-tani, N. Miyaura, J. Org. Chem. 1997, 62, 8024-8030; e) D. Zim, R. L. Vanusa, J. Dupont, A. L. Monteiro, Org. Lett. 2001, 3, 3049-3051.
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For nickel-catalyzed reactions, see: a) D. Zim, A. L. Monteiro, Tetrahedron Lett. 2002, 43, 4009-4011; b) B. H. Lipshutz, Adv. Synth. Catal. 2001, 343, 313-326; c) B. H. Lipshutz, J. A. Sclafani, P. A. Blomgren, Tetrahedron 2000, 56, 2139-2144; d) S. Saito, S. Oh-tani, N. Miyaura, J. Org. Chem. 1997, 62, 8024-8030; e) D. Zim, R. L. Vanusa, J. Dupont, A. L. Monteiro, Org. Lett. 2001, 3, 3049-3051.
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0242402659
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[5]), however, chelating phosphines such as dppf can be used.
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11
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0242570014
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note
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3500 ppm of palladium and 1160 ppm of iron.
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36
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0242486019
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note
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We found that many commercial samples of Pd/C were catalysts for this cross-coupling. We used a dry, 5% Pd/C (C6064) from Engelhard and water wet 5% Pd/C (A405023-5) and 10% Pd/C (A402032-10) catalysts from Johnson Matthey in this study.
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39
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0242570015
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note
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[6d] Our sample filtration would not remove these nanosized Pd particles, however, in the same paper they report that these Pd colloids undergo quantitative oxidative-addition by stoichiometric iodobenzene. In our system, the bromoquinoline 1 concentration is always greater than the palladium concentration which would make the presence of palladium nanoparticles unlikely.
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40
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0039926750
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Initially, the increase in Pd concentration follows the increase in the coupled product 3. We do not feel that the product 3 is causing the solubilization of the Pd because the Pd level goes through a maximum and then decreases when the concentration of 3 is the greatest. Also, heteroatoms that coordinate to transition metals often retard the cross-coupling reaction. Additionally, no N-coordinated Pd complexes were observed during an ESI-MS study of the Suzuki-Miyaura cross-coupling of pyridyl halides; see: A. O. Aliprantis, J. W. Canary, J. Am. Chem. Soc. 1994, 116, 6985-6986.
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44
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0242570018
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note
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[10] concluded during their study of the Heck reaction that leaching and redeposition of supported Pd occured and that the concentration of Pd was related to the concentration of starting materials.
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46
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0242570017
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note
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2K, however, preliminary NMR studies indicate that the reaction of boronic acid 2 with KF generates 6 species; L. M. DiMichele, unpublished results.
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