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Volumn 13, Issue 5, 2011, Pages 912-915

Reductive alkylation of indoles with alkynes and hydrosilanes under indium catalysis

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; INDIUM; INDOLE DERIVATIVE; SILANE DERIVATIVE;

EID: 79952172286     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1029673     Document Type: Article
Times cited : (51)

References (38)
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    • Use of simple aliphatic terminal alkenes causes some undesired reactions on the alkene, i.e., isomerization of the C=C bond, formation of regioisomers, and rearrangement of alkyl groups: Zhang, Z.; Wang, X.; Widenhoefer, R. A. Chem. Commun. 2006, 3717-3719
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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
    • 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
    • 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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    • 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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    • 2O (40%), n -decane (9%).
    • 2O (40%), n -decane (9%).
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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.
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    • 2O reportedly coordinates to a silicon center. For example
    • 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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    • 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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    • 2O.
    • 2O.
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