Regioselective Synthesis of 3-Alkylindoles Mediated by Zinc Triflate

Zinc triflate was found to be an effective reagent for the C3-alkylation of indoles by alkyl halides in the presence of Hünig's base and tetrabutylammonium iodide. This new method for indole alkylation proceeds by a SN1-like pathway, and is general for allylic, benzylic, and tertiary halides.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 67; no. 8; pp. 2705 - 2708
Main Authors Zhu, Xiuwen, Ganesan, A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.04.2002
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
TRYPTOPHANS
3-SUBSTITUTED INDOLES
Zinc Organic compounds
Regioselectivity
Benzylic compound
Nitrogen heterocycle
Indole
Transition metal
SN1 mechanism
Indole derivatives
Chemical synthesis
Alkylation
Allylic compound
Halogen Organic compounds
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Summary:Zinc triflate was found to be an effective reagent for the C3-alkylation of indoles by alkyl halides in the presence of Hünig's base and tetrabutylammonium iodide. This new method for indole alkylation proceeds by a SN1-like pathway, and is general for allylic, benzylic, and tertiary halides.
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ark:/67375/TPS-T3DM30TS-4
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo010996b