Nucleophilic Pentafluorophenylation of Nitroalkenes

Abstract

The interaction of pentafluorophenylmagnesium bromide with conjugate nitroalkenes is described. The optimized conditions involve performing the reaction either in diethyl ether in the presence of chlorotrimethylsilane or in a tetrahydrofuran–diethyl ether solvent mixture. The addition products can be transformed into 4,5,6,7-tetrafluoroindolines by means of a reduction and cyclization sequence.

Key words

alkenes - nucleophilic addition - fluorine - nitro compounds - pentafluorophenyl

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