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Although Terada and Sorimachi have reported addition of indoles to enamines as electron-rich alkenes, the mechanistic study indicates that imines produced in situ by isomerization of the enamine are actual acceptors of the indole: Terada, M.; Sorimachi, K. J. Am. Chem. Soc. 2007, 129, 292-293
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A part of this research was presented at the 89th annual meeting of the Chemical Society of Japan on March 29, 2009 (presentation #3F2-53). During the course of this research, two research groups reported alkylation of indoles with alkynes. However, their research profiles are different from ours
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A part of this research was presented at the 89th annual meeting of the Chemical Society of Japan on March 29, 2009 (presentation #3F2-53). During the course of this research, two research groups reported alkylation of indoles with alkynes. However, their research profiles are different from ours. Barluenga, J.; Fernández, A.; Rodríguez, F.; Fañanás, F. J. Chem.-Eur. J. 2009, 15, 8121-8123
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56749149534
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For our recent reports on indium-catalyzed carbon-carbon bond-forming reaction with indoles as nucleophiles
-
For our recent reports on indium-catalyzed carbon-carbon bond-forming reaction with indoles as nucleophiles, see: Tsuchimoto, T.; Matsubayashi, H.; Kaneko, M.; Nagase, Y.; Miyamura, T.; Shirakawa, E. J. Am. Chem. Soc. 2008, 130, 15823-15835
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79952151148
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2O (40%), n -decane (9%).
-
2O (40%), n -decane (9%).
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29
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For a leading example, see: and references therein
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79952149878
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Ratios of 4 and other possible regioisomers were assessed to be >99:<1 by GC and GC-MS analyses.
-
Ratios of 4 and other possible regioisomers were assessed to be >99:<1 by GC and GC-MS analyses.
-
-
-
-
32
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11844297848
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2O reportedly coordinates to a silicon center. For example
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2O reportedly coordinates to a silicon center. For example, see: Kobayashi, J.; Kawaguchi, K.; Kawashima, T. J. Am. Chem. Soc. 2004, 126, 16318-16319
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79952147611
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We have also previously observed that indoles with a (hetero)aryl group at the C2 position add to phenylacetylene under indium catalysis to give alkenylindoles such as 8. See ref 11a.
-
We have also previously observed that indoles with a (hetero)aryl group at the C2 position add to phenylacetylene under indium catalysis to give alkenylindoles such as 8. See ref 11a.
-
-
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-
34
-
-
79952152825
-
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2O.
-
2O.
-
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35
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0142074710
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For indium-catalyzed double addition of heteroarenes to alkynes, see
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For indium-catalyzed double addition of heteroarenes to alkynes, see: Tsuchimoto, T.; Hatanaka, K.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2003, 2454-2455
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3)-C(indolyl) bond cleavage
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3)-C(indolyl) bond cleavage, see: Deb, M. L.; Bhuyan, P. J. Synlett 2008, 325-328
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Deb, M.L.1
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