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

Research output: Contribution to journalArticle

7 Citations (Scopus)

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.
LanguageEnglish
Pages8328-8339
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number24
Early online date15 Sep 2011
DOIs
Publication statusPublished - 2011

Fingerprint

Trifluoroethanol
ambient temperature
reagents
Derivatives
acetals
Acetals
Temperature
Carbamates
Ice
synthesis
Baths
halides
baths
ice
temperature

Keywords

  • trifluoroethanol
  • aryl halides
  • one pot procedure

Cite this

Kyne, Sara H ; Percy, Jonathan M ; Pullin, Robert D C ; Redmond, Joanna M ; Wilson, Peter G. / One-pot near-ambient temperature syntheses of aryl(difluoroenol) derivatives from trifluoroethanol. In: Organic and Biomolecular Chemistry. 2011 ; Vol. 9, No. 24. pp. 8328-8339.
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One-pot near-ambient temperature syntheses of aryl(difluoroenol) derivatives from trifluoroethanol. / Kyne, Sara H; Percy, Jonathan M; Pullin, Robert D C; Redmond, Joanna M; Wilson, Peter G.

In: Organic and Biomolecular Chemistry, Vol. 9, No. 24, 2011, p. 8328-8339.

Research output: Contribution to journalArticle

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T1 - One-pot near-ambient temperature syntheses of aryl(difluoroenol) derivatives from trifluoroethanol

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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

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SP - 8328

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JO - Organic and Biomolecular Chemistry

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