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

90 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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10.1021/ol201413r

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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.\}",

year = "2011",

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doi = "10.1021/ol201413r",

language = "English",

volume = "13",

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journal = "Organic Letters",

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T1 - The benzyne Fischer-indole reaction

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

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/79960187080

U2 - 10.1021/ol201413r

DO - 10.1021/ol201413r

M3 - Article

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AN - SCOPUS:79960187080

SN - 1523-7060

VL - 13

SP - 3667

EP - 3669

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

The benzyne Fischer-indole reaction

Abstract

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