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For recent reviews on biaryl synthesis through C-H bond arylation of aromatic compounds, see: a
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For recent reviews on biaryl synthesis through C-H bond arylation of aromatic compounds, see: (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
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In the metal-catalyzed direct C-H bond arylation chemistry, electron-deficient nitrogen heterocycles are still challenging substrates, a Mukhopadhyay, S, Rothenberg, G, Gitis, D, Baidossi, M, Ponde, D. E, Sasson, Y. J. Chem. Soc, Perkin Trans. 2 2000, 1809
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In the metal-catalyzed direct C-H bond arylation chemistry, electron-deficient nitrogen heterocycles are still challenging substrates, (a) Mukhopadhyay, S.; Rothenberg, G.; Gitis, D.; Baidossi, M.; Ponde, D. E.; Sasson, Y. J. Chem. Soc., Perkin Trans. 2 2000, 1809.
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14644427257
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Although we hold the temperature at 50 °C, this is the bulk temperature of the reaction mixture. As well documented, we assume that the reaction is taking place at high-temperature hotspots that are generated by microwave irradiation, For reviews on the use of microwave in organic synthesis, see: (a) de la Hoz, A, Díaz-Oritiz, Á, Moreno, A. Chem. Soc. Rev. 2005, 34, 164
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Although we hold the temperature at 50 °C, this is the bulk temperature of the reaction mixture. As well documented, we assume that the reaction is taking place at high-temperature "hotspots" that are generated by microwave irradiation, For reviews on the use of microwave in organic synthesis, see: (a) de la Hoz, A.; Díaz-Oritiz, Á.; Moreno, A. Chem. Soc. Rev. 2005, 34, 164.
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29
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0006955301
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These results imply that our reaction does not proceed through aryne intermediates, although such a mechanism cannot be rigorously excluded at this stage, (a) Bates, R. B.; Janda, K. D. J. Org. Chem. 1982, 47, 4374.
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These results imply that our reaction does not proceed through aryne intermediates, although such a mechanism cannot be rigorously excluded at this stage, (a) Bates, R. B.; Janda, K. D. J. Org. Chem. 1982, 47, 4374.
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(b) Beller, M.; Breindl, C.; Riermeier, T. H.; Eichberger, M.; Trauthwein, H. Angew. Chem., Int. Ed. 1998, 37, 3389.
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Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. D. J. Org. Chem. 2005, 70, 161.
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32
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84868899349
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tBu similarly.
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tBu similarly.
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33
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61349142326
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See Supporting Information for details
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See Supporting Information for details.
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34
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0002523168
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Renaud, P, Sibi, M. P, Eds, Wiley-VCH: Weinheim
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Studer, A.; Bossart, M. Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, p 62.
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(b) Dichiarante, V.; Fagnoni, M.; Albini, A. Angew. Chem., Int. Ed. 2007, 46, 6495.
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35348998959
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For the selected examples using t-butoxides and haloarenes in C-H bond arylation reactions, see: (a) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
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For the selected examples using t-butoxides and haloarenes in C-H bond arylation reactions, see: (a) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
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(b) Proch, S.; Kempe, R. Angew. Chem., Int. Ed. 2007, 46, 3135.
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61349171780
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Reference 8
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(c) Reference 8.
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0037047555
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(d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553.
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48
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61349088470
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t-Butoxides are typical bases in the arylation of amines and alcohols using haloarenes. For a review, see: (a) Hang, L.; Buchwald, S. L. Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; Chapter 13.
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t-Butoxides are typical bases in the arylation of amines and alcohols using haloarenes. For a review, see: (a) Hang, L.; Buchwald, S. L. Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; Chapter 13.
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49
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0345255658
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tBu-promoted) reactions, see: (b) Shi, L.; Wang, M.; Fan. C.-A.; Zhang, F.-M.; Tu, Y.-Q. Org. Lett. 2003, 5, 3515.
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tBu-promoted) reactions, see: (b) Shi, L.; Wang, M.; Fan. C.-A.; Zhang, F.-M.; Tu, Y.-Q. Org. Lett. 2003, 5, 3515.
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