The ketene-surrogate coupling: Catalytic conversion of aryl iodides into aryl ketenes through ynol ethers

Wenhan Zhang; Joseph M. Ready

doi:10.1002/anie.201405036

The ketene-surrogate coupling: Catalytic conversion of aryl iodides into aryl ketenes through ynol ethers

Wenhan Zhang, Joseph M. Ready

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

26 Scopus citations

Abstract

tert-Butoxyacetylene is shown to undergo Sonogashira coupling with aryl iodides to yield aryl-substituted tert-butyl ynol ethers. These intermediates participate in a [1,5]-hydride shift, which results in the extrusion of isobutylene and the generation of aryl ketenes. The ketenes are trapped in situ with multiple nucleophiles or undergo electrocyclic ring closure to yield hydroxynaphthalenes and quinolines.

Original language	English (US)
Pages (from-to)	8980-8984
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	34
DOIs	https://doi.org/10.1002/anie.201405036
State	Published - Aug 18 2014

Keywords

arenes
cross-coupling
ketenes
palladium
synthetic methods

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201405036

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title = "The ketene-surrogate coupling: Catalytic conversion of aryl iodides into aryl ketenes through ynol ethers",

abstract = "tert-Butoxyacetylene is shown to undergo Sonogashira coupling with aryl iodides to yield aryl-substituted tert-butyl ynol ethers. These intermediates participate in a [1,5]-hydride shift, which results in the extrusion of isobutylene and the generation of aryl ketenes. The ketenes are trapped in situ with multiple nucleophiles or undergo electrocyclic ring closure to yield hydroxynaphthalenes and quinolines.",

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author = "Wenhan Zhang and Ready, {Joseph M.}",

year = "2014",

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doi = "10.1002/anie.201405036",

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journal = "Angewandte Chemie - International Edition",

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T1 - The ketene-surrogate coupling

T2 - Catalytic conversion of aryl iodides into aryl ketenes through ynol ethers

AU - Zhang, Wenhan

AU - Ready, Joseph M.

PY - 2014/8/18

Y1 - 2014/8/18

N2 - tert-Butoxyacetylene is shown to undergo Sonogashira coupling with aryl iodides to yield aryl-substituted tert-butyl ynol ethers. These intermediates participate in a [1,5]-hydride shift, which results in the extrusion of isobutylene and the generation of aryl ketenes. The ketenes are trapped in situ with multiple nucleophiles or undergo electrocyclic ring closure to yield hydroxynaphthalenes and quinolines.

AB - tert-Butoxyacetylene is shown to undergo Sonogashira coupling with aryl iodides to yield aryl-substituted tert-butyl ynol ethers. These intermediates participate in a [1,5]-hydride shift, which results in the extrusion of isobutylene and the generation of aryl ketenes. The ketenes are trapped in situ with multiple nucleophiles or undergo electrocyclic ring closure to yield hydroxynaphthalenes and quinolines.

KW - arenes

KW - cross-coupling

KW - ketenes

KW - palladium

KW - synthetic methods

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DO - 10.1002/anie.201405036

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VL - 53

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EP - 8984

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 34

ER -

The ketene-surrogate coupling: Catalytic conversion of aryl iodides into aryl ketenes through ynol ethers

Abstract

Keywords

ASJC Scopus subject areas

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