FeCl3 center dot 6H(2)O-Catalyzed Alkenylation of Indoles with Aldehydes

FeCl3 center dot 6H(2)O-catalyzed efficient C3-alkenylation of indoles was realized through the condensation of aldehydes and indole derivatives in the presence of 2 equiv of ethanol at ambient temperature, forming 3-vinylindoles in up to 93% yields. Ethanol promoted formation of the desired product...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 77; no. 18; pp. 8355 - 8361
Main Authors Yang, Qin, Wang, Liandi, Guo, Tenglong, Yu, Zhengkun
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 21.09.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CATALYZED REACTIONS
COUPLING REACTIONS
1,3-DICARBONYL COMPOUNDS
C2-ALKENYLATION
PYRROLES
FRIEDEL-CRAFTS ALKYLATION
C-H FUNCTIONALIZATION
EFFICIENT
DERIVATIVES
CYCLIZATION
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Summary:FeCl3 center dot 6H(2)O-catalyzed efficient C3-alkenylation of indoles was realized through the condensation of aldehydes and indole derivatives in the presence of 2 equiv of ethanol at ambient temperature, forming 3-vinylindoles in up to 93% yields. Ethanol promoted formation of the desired products. An obvious solvent effect was observed, and bisindoles were identified as the reaction intermediates.
ISSN:0022-3263
DOI:10.1021/jo301416s