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-
(a) These secondary transformations include the oxidation of organosilanes10b and organoboranes and the cross-coupling of alkenylsilanes,10c alkenylstannanes,10d and organoboranes.10e
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2442647188
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1H NMR.
-
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42
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2442707241
-
-
note
-
We cannot rule out a structure for 5 in which the α -(triethylsilyl)methyl group and the terminus of the complexed olefin have a cis relationship. However, if this were the case, cis to trans isomerization must precede conversion of 5 to 6, and this isomerization must be fast relative to the conversion of 5 to 6 as the rate of conversion of 5 to 6 was independent of [NCAr].
-
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44
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2442703588
-
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note
-
t = 0.0196 M (95% conversion).27b
-
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50
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-
0002664833
-
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Chapman, N. B., Shorter, J., Eds.; Plenum: New York
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2442703590
-
-
note
-
The principle source of error in our kinetic measurements was determination of catalyst concentration, which stemmed from the difficulty in accurately weighing 2b into the NMR tube. Efforts to improve the accuracy of these measurements by employing stock solutions of 2b were unsuccessful due to the short lifetime of 2b in solution at ambient temperature.
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77
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2442648488
-
-
note
-
2 group in the transition state [for the β-migratory insertion of 13], especially the former, make the transition state potentially quite atypical."46b
-
-
-
-
78
-
-
2442657285
-
-
note
-
-1 relative to the corresponding acyclic alkyl complex.
-
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81
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0001362368
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(c) Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424.
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Guo, Z.1
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Wang, X.; Stankovich, S. Z.; Widenhoefer, R. A. Organometallics 2002, 21, 901.
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Wang, X.1
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84
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0035477045
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Cámpora, J.1
Gutiérrez-Puebla, E.2
López, J.A.3
Monge, A.4
Palma, P.5
Del Rio, D.6
Carmona, E.7
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86
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0000215451
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(b) Berger, B. J. Santarsiero, B. D.; Trimmer, M. S. Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 3134.
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Trimmer, M.S.3
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-
87
-
-
2442714589
-
-
note
-
2 was consistent with orientation of the olefin in or near the coordination plane, and for this reason, no significant olefin rotation or reorganization of the pentenyl chain was required for olefin β-migratory insertion?.46b
-
-
-
-
89
-
-
0003487210
-
-
University Science Books: Mill Valley, CA
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(b) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
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Collman, J.P.1
Hegedus, L.S.2
Norton, J.R.3
Finke, R.G.4
-
90
-
-
2442718401
-
-
note
-
‡ for the conversion of 5 to 6 relative to the conversion of 14 to 15 is due to migration of a Pd-secondary alkyl group in the case of 5 and a palladium-primary alkyl group in the case of 14.
-
-
-
-
91
-
-
2442703589
-
-
note
-
1H NMR analysis under these conditions.
-
-
-
-
93
-
-
0000314404
-
-
Svensson, M.; Matsubara, T.; Morokuma, K. Organometallics 1996, 15, 5568.
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Svensson, M.1
Matsubara, T.2
Morokuma, K.3
-
94
-
-
2442664744
-
-
note
-
Alternatively, Pd-C bond cleavage could occur via an oxidative addition/reductive elimination sequence.
-
-
-
-
95
-
-
2442710924
-
-
note
-
3) generated in the catalytic silane competition experiments.
-
-
-
-
96
-
-
2442653472
-
-
note
-
3 formed (3,3-dimethylbutyl)triethylsilane to the exclusion of (3,3-dimethylbutyl)triphenylsilane,14 which indicates that olefin insertion/silylation of 4e is much faster than is silyl exchange. Because NCAr and an olefin of 1 are of comparable ligating ability with respect to cationic Pd(II) complexes,36 this result strongly suggests that 4b does not undergo silyl exchange prior to conversion to 5.
-
-
-
-
97
-
-
2442696003
-
-
note
-
‡ should be destabilized by the decreasing electron density and increasing steric bulk of the silane.
-
-
-
-
98
-
-
2442710923
-
-
note
-
1/2 = 22 min at -41 °C) ensures rapid activation of precatalyst 2b relative to catalyst turnover.
-
-
-
-
99
-
-
2442688615
-
-
note
-
3 corresponds to a macroscopic rate constant for the conversion of 6 to 4b for the specific case where [NCAr] = 42 mM.
-
-
-
|