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(a) Campeau, L.-C.; Stuart, D. R.; Leclerc, J.-P.; Bertrand-Laperle, M.; Villermure, E; Sun, H.-Y.; Lasserre, S.; Guimond, N.; Lecavallier, M.; Fagnou, K. J. Am. Chem Soc. 2009, 131, 3291.
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77949828962
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A multikilogram process based on this system was run successfully.
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A multikilogram process based on this system was run successfully.
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23
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0035901659
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2 are competent palladium catalyst partners.
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2 are competent palladium catalyst partners.
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Li, G.Y.1
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24
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77949839088
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3CN.
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3CN.
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25
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77949842762
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The coupling experiment using 0.25 mol % Pd and Xantphos in the absence of 1 gave <5% product.
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The coupling experiment using 0.25 mol % Pd and Xantphos in the absence of 1 gave <5% product.
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26
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77949821356
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IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene.
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IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene.
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27
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31544455027
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Similar controversial poor reactivity of aryl iodides in C-H arylation has recently been observed: Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581.
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28
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50249118513
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1H NMR studies showed strong binding of 2 with the former to form the corresponding complex, but the analogous interaction was not observed with the latter. A similar explanation has been proposed in N-oxide C-H arylations. See: Gorelsky, S. L; Lapointe, D.; Fagnou, K. J. Am. Chem. 2008, 130, 10848.
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77949805346
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D = 1.3) indicates that deprotonation is unlikely to be the rate-determining step.
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D = 1.3) indicates that deprotonation is unlikely to be the rate-determining step.
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30
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0035200787
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The Xantphos bite angle may play a crucial role: Kamer, P. C.; Van Leeuwen, P. W. N. M.; Reek, J. N. H. Acc. Chem. Res. 2001, 34, 895.
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A similar mechanism was proposed in Pd/Cu-catalyzed decarboxylative coupling: Goossen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662.
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