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34
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58149190430
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A tentative possibility is that triethylsilane undergoes nickel-catalyzed conversion to triethylsilanol in the presence of water to generate the Et 3SiX species depicted in Scheme 3. Control experiments illustrated that Et3SiOH is slowly produced under the reaction conditions in the absence of substrate 2
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3SiOH is slowly produced under the reaction conditions in the absence of substrate 2.
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35
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58149198781
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For a detailed study of the role of the acceleration of oxidative cyclizations by Lewis acids see: Hratchian. H. P.; Chowdhury. S. K.; Gutiérre;z-García, V. M.; Amarasinghe. K. K. D.; Heeg, M. J.; Schlegel, H. B.; Montgomery, J. Organometallics 2004, 23, 4636.
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(a) For a detailed study of the role of the acceleration of oxidative cyclizations by Lewis acids see: Hratchian. H. P.; Chowdhury. S. K.; Gutiérre;z-García, V. M.; Amarasinghe. K. K. D.; Heeg, M. J.; Schlegel, H. B.; Montgomery, J. Organometallics 2004, 23, 4636.
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36
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0033082780
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For an earlier suggestion of Lewis acid catalysis of metallacycle generation see
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(b) For an earlier suggestion of Lewis acid catalysis of metallacycle generation see: Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata. K.; Shimizu. M.; Matsumoto, S.; Tamara, Y. Angew. Chem., Int. Ed. 1999, 38, 397.
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Kimura, M.1
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Tamara, Y.7
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37
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58149198782
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Simple intermolecuiar reductive couplings of benzaldehyde with either styrene or allyl benzene are not promoted by either Et3SiH in wet THF or Et3SiOH in dry THF with use of the catalyst and reaction conditions used in the production of 10
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3SiOH in dry THF with use of the catalyst and reaction conditions used in the production of 10.
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38
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58149198180
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Additional synthetic manipulations of compounds derived from 19 were performed for the confirmation of structure 20. See the Supporting Information for details.
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Additional synthetic manipulations of compounds derived from 19 were performed for the confirmation of structure 20. See the Supporting Information for details.
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