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For a summation of studies of transmetalation in the Suzuki-Miyaura reaction, see
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9
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For data that are consistent with transmetalation by a mechanism involving reaction of a boronic acid with a palladium hydroxide, see: (a)
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For data that are consistent with transmetalation by a mechanism involving reaction of a boronic acid with a palladium hydroxide, see: (a) Suzaki, Y.; Osakada, K. Organometallics 2006, 25, 3251-3258.
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(b) Siegmann, K.; Pregosin, P. S.; Venanzi, L. M. Organometallics 1989, 8, 2659-2664.
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(d) Kakino, R.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2001, 74, 371-376.
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Kakino, R.1
Shimizu, I.2
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13
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34247477344
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For studies that highlight the frequent ambiguity of the turnoverlimiting step of the Suzuki-Miyaura reaction, see: (a)
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For studies that highlight the frequent ambiguity of the turnoverlimiting step of the Suzuki-Miyaura reaction, see: (a) Espino, G.; Kurbangalieva, A.; Brown, J. M. Chem. Commun. 2007, 1742-1744.
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Espino, G.1
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(b) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550-9561.
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(c) Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818-11819.
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(d) Lu, Z.; Fu, G. C. Angew. Chem., Int. Ed. 2010, 49, 6676-6678.
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Lu, Z.1
Fu, G.C.2
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19
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Cammidge, A. N.; Goddard, V. H. M.; Gopee, H.; Harrison, N. L.; Hughes, D. L.; Schubert, C. J.; Sutton, B. M.; Watts, G. L.; Whitehead, A. J. Org. Lett. 2006, 8, 4071-4074.
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Cammidge, A.N.1
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Sutton, B.M.7
Watts, G.L.8
Whitehead, A.J.9
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20
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79951830779
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note
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Yields for organic products were determined by GC analysis versus n-tetradecane as internal standard.
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21
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79951819025
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note
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A similar reaction was reported previously with no experimental details in reviews by Suzuki and Miyaura. See ref 9.
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23
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0002812967
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Miyaura, N., Ed.; Springer: Berlin/Heidelberg
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(b) Miyaura, N. In Cross-Coupling Reactions; Miyaura, N., Ed.; Springer: Berlin/Heidelberg: 2002; Vol. 219, p 11-59.
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Miyaura, N.1
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24
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79951830183
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note
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Aqueous THF mixtures are biphasic in the presence of inorganic base, whereas aqueous acetone mixtures remain homogeneous.
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25
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77954846356
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Butters, M.; Harvey, J.; Jover, J.; Lennox, A.; Lloyd-Jones, G.; Murray, P. Angew. Chem., Int. Ed. 2010, 49, 5156-5160.
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Lloyd-Jones, G.5
Murray, P.6
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26
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79951848285
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note
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Lloyd-Jones et al. also reported that the population of free boronic acid increases when the concentration of water is decreased.
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29
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0942298035
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(b) Stambuli, J. P.; Incarvito, C. D.; Bühl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 1184-1194.
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(c) Huser, M.; Youinou, M. T.; Osborn, J. A. Angew. Chem. 1989, 101, 1427-1430.
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0001600288
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(d) Ozawa, F.; Kawasaki, N.; Okamoto, H.; Yamamoto, T.; Yamamoto, A. Organometallics 1987, 6, 1640-1651.
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Ozawa, F.1
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Okamoto, H.3
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Yamamoto, A.5
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32
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79951819024
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note
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3)4 upon warming.
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