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(i) Edwards, D. R.; Hleba, Y. B.; Lata, C. J.; Calhoun, L. A.; Crudden, C. M. Angew. Chem., Int. Ed. 2007, 46, 7799-7802.
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55249084804
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The screening of ligands clarified the notion that DPPB is suitable for the regioselectivity in the present catalysis. Other ligands diminished the regioselectivity in some cases: see the Supporting Information
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The screening of ligands clarified the notion that DPPB is suitable for the regioselectivity in the present catalysis. Other ligands diminished the regioselectivity in some cases: see the Supporting Information.
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2 in pinacolborane was suggested by: Shimada, S.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Angew. Chem., Int. Ed. 2001, 40, 2168-2171.
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2 in pinacolborane was suggested by: Shimada, S.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Angew. Chem., Int. Ed. 2001, 40, 2168-2171.
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(a) Dai, C.; Robins, E. G.; Scott, A. J.; Clegg, W.; Yufit, D. S.; Howard, J. A. K.; Marder, T. B. Chem. Commun. 1998, 1983-1984.
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Dai, C.1
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Yufit, D.S.5
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0345356309
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The use of catecholborane (HBcat) under the same reaction conditions as entry 5, Table 1 gave a mixture of 1-phenylethanol and 2-phenylethanol in 82% yield with 93/7 ratio after the oxidation of the crude boronate compounds. The preceding reports detailed the difference between HBpin and HBcat; see ref 3i and: Lam, W. H, Shimada, S, Batsanov, A. S, Lin, Z, Marder, T. B, Cowan, J. A, Howard, J. A. K, Mason, S. A, McIntyre, G. J. Organometallics 2003, 22, 4557-4568. A mechanistic investigation will be carried out in due course in future studies
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The use of catecholborane (HBcat) under the same reaction conditions as entry 5, Table 1 gave a mixture of 1-phenylethanol and 2-phenylethanol in 82% yield with 93/7 ratio after the oxidation of the crude boronate compounds. The preceding reports detailed the difference between HBpin and HBcat; see ref 3i and: Lam, W. H.; Shimada, S.; Batsanov, A. S.; Lin, Z.; Marder, T. B.; Cowan, J. A.; Howard, J. A. K.; Mason, S. A.; McIntyre, G. J. Organometallics 2003, 22, 4557-4568. A mechanistic investigation will be carried out in due course in future studies.
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55249083649
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The reaction in the presence of low catalyst loading should be conducted under precisely dehydrated conditions; the decomposition of HBpin with H 2O causes decreasing regioselectivity
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2O causes decreasing regioselectivity.
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27
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0001411843
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(a) Westcott, S.; Marder, T. B.; Baker, R. T. Organometallics 1993, 12, 975-979.
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(1993)
Organometallics
, vol.12
, pp. 975-979
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Westcott, S.1
Marder, T.B.2
Baker, R.T.3
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55249100882
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Other counteranions, such as pivalate and benzoate, gave similar results
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Other counteranions, such as pivalate and benzoate, gave similar results.
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55249086862
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The reaction in DMSO as a solvent gave better results in some cases. The details are described in the Supporting Information
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The reaction in DMSO as a solvent gave better results in some cases. The details are described in the Supporting Information.
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31
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55249120335
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The reaction of a 1,1-disubstituted ethylene, such as a-methylstyrene, gave a mixture of regioisomers. We have not examined the reaction of trisubstituted ethylenes due to insufficient regioselectivity
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The reaction of a 1,1-disubstituted ethylene, such as a-methylstyrene, gave a mixture of regioisomers. We have not examined the reaction of trisubstituted ethylenes due to insufficient regioselectivity.
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55249091260
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31P NMR experiments were examined; however, the precise characterization of the Rh(III) intermediate is difficult. Details of the NMR experiments are described in the Supporting Information. Further investigation is ongoing to clarify Rh(III) intermediates.
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31P NMR experiments were examined; however, the precise characterization of the Rh(III) intermediate is difficult. Details of the NMR experiments are described in the Supporting Information. Further investigation is ongoing to clarify Rh(III) intermediates.
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0001008441
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Irvine. G. J.; Lesley. M. J. G.; Marder, T. B.; Norman, N. C.; Rice, C. R.; Robins, E. G.; Roper, W. R.; Whittell, G. R.; Wright, L. J. Chem. Rev. 1998, 98, 2685-2722.
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(1998)
Chem. Rev
, vol.98
, pp. 2685-2722
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Irvine, G.J.1
Lesley, M.J.G.2
Marder, T.B.3
Norman, N.C.4
Rice, C.R.5
Robins, E.G.6
Roper, W.R.7
Whittell, G.R.8
Wright, L.J.9
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34
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55249101117
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Iacac did not promote the reaction at all (entry 3, Table 1). In addition, the distilled HBpin can promote the present reaction. The generation of a borate-Rh(I) complex does not seem to be essential.
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Iacac did not promote the reaction at all (entry 3, Table 1). In addition, the distilled HBpin can promote the present reaction. The generation of a borate-Rh(I) complex does not seem to be essential.
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2 Hayashi, T.; Takahashi, M.; Takaya. Y.; Ogasawara, M. J. Am. Chem. Soc. 2002. 124, 5052-5058.
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2 Hayashi, T.; Takahashi, M.; Takaya. Y.; Ogasawara, M. J. Am. Chem. Soc. 2002. 124, 5052-5058.
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