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Regioselective synthesis of 3-alkylindoles mediated by zinc triflate

Regioselective synthesis of 3-alkylindoles mediated by zinc triflate
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 Hunig's base and tetrabutylammonium iodide. This new method for indole alkylation proceeds by a S(N)1-like pathway, and is general for allylic, benzylic, and tertiary halides.
3-substituted indoles, tryptophans
0022-3263
2705-2708
Zhu, X. W.
fad0ac04-78c6-4a45-820d-67b55e1a362b
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9
Zhu, X. W.
fad0ac04-78c6-4a45-820d-67b55e1a362b
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9

Zhu, X. W. and Ganesan, A. (2002) Regioselective synthesis of 3-alkylindoles mediated by zinc triflate. Journal of Organic Chemistry, 67 (8), 2705-2708. (doi:10.1021/jo010996b).

Record type: Article

Abstract

Zinc triflate was found to be an effective reagent for the C3-alkylation of indoles by alkyl halides in the presence of Hunig's base and tetrabutylammonium iodide. This new method for indole alkylation proceeds by a S(N)1-like pathway, and is general for allylic, benzylic, and tertiary halides.

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More information

Published date: 19 April 2002
Keywords: 3-substituted indoles, tryptophans

Identifiers

Local EPrints ID: 19873
URI: http://eprints.soton.ac.uk/id/eprint/19873
ISSN: 0022-3263
PURE UUID: 7ef5f926-239a-4e91-8392-17f20e6481c7

Catalogue record

Date deposited: 20 Feb 2006
Last modified: 15 Mar 2024 06:20

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Contributors

Author: X. W. Zhu
Author: A. Ganesan

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