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All ligands except for 3 are commercially available from Strem Chemical. (a) Kaye, S.; Fox, J. M.; Hicks, F. A.; Buchwald, S. L. Adv. Synth. Catal. 2001, 343, 789.
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(a) Rosner, T.; Le Bars, J.; Pfaltz, A.; Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 1848.
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18
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0242479003
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note
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Using ligands 1-5 the reaction in eq 1 went to >99% conversion and >98% yield.
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19
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0000151617
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For studies examining the reduction of Pd(II) to Pd(0) with amines, see: (a) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A. Organometallics 1995, 14, 1818.
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20
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0242395600
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(b) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAllees, A. J.; Stephenson, D. K. J. Chem. Res. Synop. 1984, 360.
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21
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0242479000
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note
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The intrinsic activity of ligand 1 is probably even greater than suggested by the data in Figure 1 because at the catalyst concentrations employed in this experiment its reaction rate approaches the limit of detection of the reaction calorimeter.
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-
-
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22
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0242479001
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note
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Decreasing consecutive initial rates for reactions with successively lower initial [amine] suggests intrinsic positive order kinetics in [amine]; however, it could also be attributed to zero-order kinetics in [amine] and decreasing [catalyst] due to catalyst deactivation.
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23
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0242647365
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note
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2Pd(II) complex as we propose here; see refs 4, 5, 6, and 9.
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24
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0012253713
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A similar mechanism has been proposed for the Pd-catalyzed aerobic alcohol oxidation: Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179.
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Org. Lett.
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Steinhoff, B.A.1
Stahl, S.S.2
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25
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0242479002
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note
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2, 7, and NaOt-Am resulted in only free phosphine and a small residual peak that cannot be identified at 48 ppm: no phosphine oxide was present in either mixture. Thus, it is difficult to draw conclusions on the basis of these studies.
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26
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0030007033
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For examples of β-hydride elimination from Pd(II)-amido complexes, see: (b) Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626.
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0020793135
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(e) Murahashi, S. I.; Yoshimura, T.; Tsumiyama, T.; Kojima, T. J. Am. Chem. Soc. 1983, 105, 5002.
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31
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33748621833
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3 as the catalyst and NaOt-Bu as the base, see: Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
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Guram, A.S.1
Rennels, R.A.2
Buchwald, S.L.3
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32
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0037125518
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Similar KIEs have been observed for β-hydride elimination from metal-alkyl and metal-alkoxide complexes: (a) Mueller, J. A.; Jensen, D. R.; Sigman, M. S. J. Am. Chem. Soc. 2002. 124, 8202.
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Mueller, J.A.1
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34
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0000798112
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And ref 10
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(c) Romeo, R.; Alibrandi, G.; Scolaro, L. M. Inorg. Chem. 1993, 32, 4688. And ref 10.
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Romeo, R.1
Alibrandi, G.2
Scolaro, L.M.3
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