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Jia, C., Lu, W., Oyamada, J., Kitamura, T., Matsuda, K., Irie, M., and Fujiwara, Y. J. Am. Chem. Soc. 2000, 122, 7252 However, futher mechanistic studies have suggested that the reaction proceeds through a Friedel-Crafts-type reaction of a metal-activated alkyne. See: Tunge, J. A. and Foresee, L. N. Organometallics 2005, 24, 6440
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77952573351
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For a screen of indole protecting groups, see the Supporting Information
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For a screen of indole protecting groups, see the Supporting Information.
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35
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2 to be a useful catalyst for the reaction of alkynes with a range of arenes: Fukutani, T., Umeda, N., Hirano, K., Satoh, T., and Miura, M. Chem. Commun. 2009, 5141
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77952565354
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Use of the dimethylcarbamoyl protecting group in this case led to poor conversion to product
-
Use of the dimethylcarbamoyl protecting group in this case led to poor conversion to product.
-
-
-
-
39
-
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77952555338
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-
Under the standard reaction conditions, terminal and dialkyl alkynes afforded only trace amounts of product
-
Under the standard reaction conditions, terminal and dialkyl alkynes afforded only trace amounts of product.
-
-
-
-
40
-
-
77952559436
-
-
See the Supporting Information for details
-
See the Supporting Information for details
-
-
-
-
41
-
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77952560621
-
-
Under the same reaction conditions, using 1a and PivOD resulted in deuterium incorporation at the alkene position. A control experiment revealed no H/D exchange at the alkene of 3a under the reaction conditions
-
Under the same reaction conditions, using 1a and PivOD resulted in deuterium incorporation at the alkene position. A control experiment revealed no H/D exchange at the alkene of 3a under the reaction conditions.
-
-
-
-
42
-
-
77952560096
-
-
Under the standard reaction conditions in the absence of catalyst, no deuterium loss was observed
-
Under the standard reaction conditions in the absence of catalyst, no deuterium loss was observed.
-
-
-
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43
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0000663764
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For an example of reactivity of a cationic metal with alkynes, see
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A competition between methoxyindole 1b and nitroindole 1c revealed a preference for the more electron-rich arene (4:1 ratio), which is consistent with C-H bond cleavage via electrophilic activation, as previously demonstrated for related systems. See
-
A competition between methoxyindole 1b and nitroindole 1c revealed a preference for the more electron-rich arene (4:1 ratio), which is consistent with C-H bond cleavage via electrophilic activation, as previously demonstrated for related systems. See: Li, L., Brennessel, W. W., and Jones, W. D. Organometallics 2009, 28, 3492
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