One-pot near-ambient temperature syntheses of aryl(difluoroenol) derivatives from trifluoroethanol

Sara H Kyne; Jonathan M Percy; Robert D C Pullin; Joanna M Redmond; Peter G Wilson

doi:10.1039/C1OB06372C

One-pot near-ambient temperature syntheses of aryl(difluoroenol) derivatives from trifluoroethanol

Sara H Kyne, Jonathan M Percy, Robert D C Pullin, Joanna M Redmond, Peter G Wilson

Pure And Applied Chemistry

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Abstract

Difluoroalkenylzinc reagents prepared from 1-(2’-methoxy-ethoxymethoxy)-2,2,2-trifluoroethane and 1-(N,N-diethylcarbamoyloxy)-2,2,2-trifluoroethane at ice bath temperatures, underwent Negishi coupling with a range of aryl halides in a convenient one pot procedure. While significant differences between the enol acetal and carbamate reagents were revealed, the Negishi protocol compared very favourably with alternative coupling procedures in terms of overall yields from trifluoroethanol.

Original language	English
Pages (from-to)	8328-8339
Number of pages	12
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	24
Early online date	15 Sept 2011
DOIs	https://doi.org/10.1039/C1OB06372C
Publication status	Published - 2011

Keywords

trifluoroethanol
aryl halides
one pot procedure

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10.1039/C1OB06372C

One pot near ambientFinal published version, 543 KB

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abstract = "Difluoroalkenylzinc reagents prepared from 1-(2{\textquoteright}-methoxy-ethoxymethoxy)-2,2,2-trifluoroethane and 1-(N,N-diethylcarbamoyloxy)-2,2,2-trifluoroethane at ice bath temperatures, underwent Negishi coupling with a range of aryl halides in a convenient one pot procedure. While significant differences between the enol acetal and carbamate reagents were revealed, the Negishi protocol compared very favourably with alternative coupling procedures in terms of overall yields from trifluoroethanol.",

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AU - Kyne, Sara H

AU - Percy, Jonathan M

AU - Pullin, Robert D C

AU - Redmond, Joanna M

AU - Wilson, Peter G

PY - 2011

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AB - Difluoroalkenylzinc reagents prepared from 1-(2’-methoxy-ethoxymethoxy)-2,2,2-trifluoroethane and 1-(N,N-diethylcarbamoyloxy)-2,2,2-trifluoroethane at ice bath temperatures, underwent Negishi coupling with a range of aryl halides in a convenient one pot procedure. While significant differences between the enol acetal and carbamate reagents were revealed, the Negishi protocol compared very favourably with alternative coupling procedures in terms of overall yields from trifluoroethanol.

KW - trifluoroethanol

KW - aryl halides

KW - one pot procedure

U2 - 10.1039/C1OB06372C

DO - 10.1039/C1OB06372C

M3 - Article

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JF - Organic and Biomolecular Chemistry

IS - 24

ER -

One-pot near-ambient temperature syntheses of aryl(difluoroenol) derivatives from trifluoroethanol

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Keywords

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