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Recent reviews: a) N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59;
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Bellina, F.1
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Eds, F. Diederich, A. de Meijere, Wiley-VCH, New York, chap.2
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c) N. Miyaura in Metal-Catalyzed Cross-Coupling Reaction (Eds.: F. Diederich, A. de Meijere), Wiley-VCH, New York, 2004, chap.2.
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23044516874
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For a review of the Suzuki-Miyaura reaction of heteroaryl nucleophiles, see
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For a review of the Suzuki-Miyaura reaction of heteroaryl nucleophiles, see: E. Tyrell, P. Brookes, Synthesis 2004, 4, 469-483.
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d) K. M. Meyers, N. Kim, J. L. Mendez-Andino, X. E. Hu, R. N. Mumin, S. R. Klopfenstein, J. A. Wos, M. C. Mitchell, J. L. Paris, D. C. Ackley, J. K. Holbert, S. W. Mittelstadt, O. Reizes, Bioorg. Med. Chem. Lett. 2007, 17, 814-818;
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0000910871
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For examples of Suzuki-Miyaura reactions of 2-pyridyl boronic acids, see: a K. Deshayes, R. D. Broene, I. Chao, C. B. Knobler, F. Diederich, J. Org. Chem. 1991, 56, 6787-6795;
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For examples of Suzuki-Miyaura reactions of 2-pyridyl boronic acids, see: a) K. Deshayes, R. D. Broene, I. Chao, C. B. Knobler, F. Diederich, J. Org. Chem. 1991, 56, 6787-6795;
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b) M. D. Sindkhedkar, H. R. Mulla, M. A. Wirth, A. Cammers-Goodwin, Tetrahedron 2001, 57, 2991-2996;
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c) S. D. Mandolesi, S. E. Vaillard, J. C. Podestá, R. A. Rossi, Organometallics 2002, 21, 4886-4888;
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d) A. Bouillon, J.-C. Lancelot, J. Sopkova de Oliveira Santos, V. Collot, P. R. Bovy, S. Rault, Tetrahedron 2003, 59, 10043-10049;
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e) T. Shinozuka, K. Shimada, S. Matsui, T. Tamane, M. Ama, T. Fukuda, M. Taki, Y. Takeda, E. Otsuka, M. Yamato, S. Naito, Bioorg. Med. Chem. 2006, 14, 6807-6819.
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Naito, S.11
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53349157513
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utilizing 2-pyridyl pinacol boronate esters. Chlorod ialkyl phosphines and dialkyl phosphine oxides were used as supporting ligands
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During the development of this work, we discovered unpublished results from CombiPhos Catalysts, Inc
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During the development of this work, we discovered unpublished results from CombiPhos Catalysts, Inc. utilizing 2-pyridyl pinacol boronate esters. Chlorod ialkyl phosphines and dialkyl phosphine oxides were used as supporting ligands. However, we found that 2-pyridyl pinacol boronate ester was not effectively coupled under our conditions as seen in Table 1.
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However, we found that 2-pyridyl pinacol boronate ester was not effectively coupled under our conditions as seen in Table
, vol.1
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18
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0348048805
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For examples of Suzuki-Miyaura reactions of 2-pyridyl N,N-diethanolamine boronate esters, see: a P. B. Hodgson, F. H. Salingue, Tetrahedron Lett. 2004, 45, 685-687;
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For examples of Suzuki-Miyaura reactions of 2-pyridyl N,N-diethanolamine boronate esters, see: a) P. B. Hodgson, F. H. Salingue, Tetrahedron Lett. 2004, 45, 685-687;
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19
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b) P. Gros, A. Doudouh, Y. Fort, Tetrahedron Lett. 2004, 45, 6239-6241.
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Fort, Y.3
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0038362703
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For work with 2-pyridyltrifluoroborates, see
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For work with 2-pyridyltrifluoroborates, see: G. A. Molander, B. Biolatto, J. Org. Chem. 2003, 68, 4302-4314.
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J. Org. Chem
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Molander, G.A.1
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Y. Yamamoto, M. Takizawa, X.-Q. Yu, N. Miyaura. Angew. Chem. 2008, 120, 942-945;
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38549118405
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Angew. Chem. Int. Ed. 2008, 47, 928-931;
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Angew. Chem. Int. Ed
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Angew. Chem. Int. Ed. 2008, 47, 928-931.
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Angew. Chem. Int. Ed
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53349155782
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For selected examples of phosphine oxides ligands in carbon-carbon bond-forming cross-coupling processes, see: a G. Y. Li, Angew. Chem. 2001, 113, 1561-1564;
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For selected examples of phosphine oxides ligands in carbon-carbon bond-forming cross-coupling processes, see: a) G. Y. Li, Angew. Chem. 2001, 113, 1561-1564;
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25
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0035901659
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Angew. Chem. Int. Ed. 2001, 40, 1513-1516;
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53349131979
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Substituted Pyridines as Selective Cyclooxygenase-2 Inhibitors: D. Dube, R. Fortin, R. Friesen, Z. Wang, J. Gauthier Merck Frost Canada Inc, WO 98/03484, 1998;
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a) "Substituted Pyridines as Selective Cyclooxygenase-2 Inhibitors": D. Dube, R. Fortin, R. Friesen, Z. Wang, J. Gauthier (Merck Frost Canada Inc.), WO 98/03484, 1998;
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b) B. T. O'Neill, D. Yohannes, M. W. Bundesmann, E. P. Arnold, Org. Lett. 2000, 2, 4201-4204;
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Arnold, E.P.4
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36
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53349150256
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Process for the Production of Quinazolines: B. Ahman, P. Hodgson, S. Lewandowski, R. Walton Pfizer Inc, WO 02/094815, 2002
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c) "Process for the Production of Quinazolines": B. Ahman, P. Hodgson, S. Lewandowski, R. Walton (Pfizer Inc.), WO 02/094815, 2002.
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37
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53349135110
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The 2-pyridylborates are somewhat air-sensitive, so they were stored in a benchtop desiccator to prolong the lifetime of the reagents. However, during the setup of each reaction, these reagents were weighed out on a bench open to the air.
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The 2-pyridylborates are somewhat air-sensitive, so they were stored in a benchtop desiccator to prolong the lifetime of the reagents. However, during the setup of each reaction, these reagents were weighed out on a bench open to the air.
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38
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0037178508
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For a related protocol for the synthesis of 3-pyridine boronic acid, see
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For a related protocol for the synthesis of 3-pyridine boronic acid, see: W. Li, D. P. Nelson, M. S. Jensen, R. S. Hoerrner, D. Cai, R. D. Larsen, P. J. Reider, J. Org. Chem. 2002, 67, 5394-5397.
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J. Org. Chem
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Li, W.1
Nelson, D.P.2
Jensen, M.S.3
Hoerrner, R.S.4
Cai, D.5
Larsen, R.D.6
Reider, P.J.7
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