The benzyne Fischer-indole reaction

Donald McAusland; Sangwon Seo; Didier G. Pintori; Jonathan Finlayson; Michael F. Greaney

doi:10.1021/ol201413r

The benzyne Fischer-indole reaction

Donald McAusland, Sangwon Seo, Didier G. Pintori, Jonathan Finlayson, Michael F. Greaney

Department of Physics and Chemistry

Research output: Contribution to journal › Article › peer-review

88 Scopus citations

Abstract

A new approach to the Fischer-indole synthesis is reported that uses the reactive intermediate benzyne. The addition of N-tosyl hydrazones to arynes, generated through fluoride activation of 2-(trimethylsilyl)phenyl triflate precursors, leads to efficient N-arylation. Addition of a Lewis acid to the same reaction pot then affords N-tosylindole products via Fischer cyclization.

Original language	English
Pages (from-to)	3667-3669
Number of pages	3
Journal	Organic Letters
Volume	13
Issue number	14
DOIs	https://doi.org/10.1021/ol201413r
State	Published - 15 Jul 2011

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title = "The benzyne Fischer-indole reaction",

abstract = "A new approach to the Fischer-indole synthesis is reported that uses the reactive intermediate benzyne. The addition of N-tosyl hydrazones to arynes, generated through fluoride activation of 2-(trimethylsilyl)phenyl triflate precursors, leads to efficient N-arylation. Addition of a Lewis acid to the same reaction pot then affords N-tosylindole products via Fischer cyclization.",

author = "Donald McAusland and Sangwon Seo and Pintori, {Didier G.} and Jonathan Finlayson and Greaney, {Michael F.}",

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AU - McAusland, Donald

AU - Seo, Sangwon

AU - Pintori, Didier G.

AU - Finlayson, Jonathan

AU - Greaney, Michael F.

PY - 2011/7/15

Y1 - 2011/7/15

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AB - A new approach to the Fischer-indole synthesis is reported that uses the reactive intermediate benzyne. The addition of N-tosyl hydrazones to arynes, generated through fluoride activation of 2-(trimethylsilyl)phenyl triflate precursors, leads to efficient N-arylation. Addition of a Lewis acid to the same reaction pot then affords N-tosylindole products via Fischer cyclization.

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The benzyne Fischer-indole reaction

Abstract

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