Synthesis of C₆F₅-Substituted Amines Containing Quaternary Carbon Atoms

Abstract

The reaction of enamines and methyltris(pentafluoro­phenyl)silane in the presence of acetic acid affording C₆F₅-substituted amines is described. The proposed mechanism features a transfer of the C₆F₅ group from the five-coordinate silicate intermediate onto an iminium cation resulting in the generation of a quaternary carbon atom in the C-C bond forming event.

Key words

amines - enamines - silicon - hypercoordination - tris(pentafluorophenyl)silyl derivatives

References

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In contrast, MeOSi(C₆F₅)₃ is prepared in several steps and is moisture-sensitive, see ref 2.