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

Kyne, Sara H and Percy, Jonathan M and Pullin, Robert D C and Redmond, Joanna M and Wilson, Peter G (2011) One-pot near-ambient temperature syntheses of aryl(difluoroenol) derivatives from trifluoroethanol. Organic and Biomolecular Chemistry, 9 (24). pp. 8328-8339. ISSN 1477-0520 (https://doi.org/10.1039/C1OB06372C)

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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.

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