Negishi coupling of metallated difluoroenol derivatives based on trifluoroethanol

Wilson, Peter and Percy, Jonathan M. and Redmond, Joanna M. (2011) Negishi coupling of metallated difluoroenol derivatives based on trifluoroethanol. Abstracts of papers - American Chemical Society, 242. FLUO-65.

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Abstract

Difluorovinylmetal building blocks prepd. from 1-(2'-methoxy-ethoxymethoxy) -2,2,2-trifluoroethane (1a) and 1-(N,N-diethylcarbamoyloxy)-2,2,2-trifluoroethane (1b), have been used in our lab. in syntheses of analogs of biol. significant compds. Access to these useful reagents requires a dehydrofluorination/metalation step at -78°C; however, the seminal work of Donald Burton and co-workers have allowed us to prep. difluorovinylzinc reagents 2a and 2b and iodides 3a and 3b at near ambient temp. and investigate their scope in palladium catalyzed coupling.