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

25 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
Chemistry(all)

Access to Document

10.1002/anie.201405036

Cite this

@article{e53ded2dca08498dab2ad38104279e4b,

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.",

keywords = "arenes, cross-coupling, ketenes, palladium, synthetic methods",

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

year = "2014",

month = aug,

day = "18",

doi = "10.1002/anie.201405036",

language = "English (US)",

volume = "53",

pages = "8980--8984",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "34",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=84906047572&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84906047572&partnerID=8YFLogxK

U2 - 10.1002/anie.201405036

DO - 10.1002/anie.201405036

M3 - Article

C2 - 24975840

AN - SCOPUS:84906047572

SN - 1433-7851

VL - 53

SP - 8980

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

Access to Document

Other files and links

Fingerprint

Cite this