Issue 24, 2011
From the journal:

Organic & Biomolecular Chemistry

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

Sara H. Kyne,a   Jonathan M. Percy,*a   Robert D. C. Pullin,‡b   Joanna M. Redmondc  and  Peter G. Wilsona  

* Corresponding authors

a WestChem Department of Pure and Applied Chemistry, Thomas Graham Building, 295 Cathedral Street, Glasgow, UK
E-mail: jonathan.percy@strath.ac.uk
Tel: +44 141 548 4398

b Department of Chemistry, University of Leicester, University Road, Leicester, UK

c Respiratory CEDD, GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, UK

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.

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

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Article information

DOI
https://doi.org/10.1039/C1OB06372C
Article type
Paper
Submitted
11 Aug 2011
Accepted
15 Sep 2011
First published
15 Sep 2011

Org. Biomol. Chem., 2011,9, 8328-8339

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

S. H. Kyne, J. M. Percy, R. D. C. Pullin, J. M. Redmond and P. G. Wilson, Org. Biomol. Chem., 2011, 9, 8328 DOI: 10.1039/C1OB06372C

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