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Synthesis 2006(3): 447-450  
DOI: 10.1055/s-2006-926277
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of C6F5-Substituted Amines Containing Quaternary Carbon Atoms

Alexander D. Dilman*, Vitalij V. Levin, Pavel A. Belyakov, Marina I. Struchkova, Vladimir A. Tartakovsky
N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation
Fax: +7(95)1355328; e-Mail: adil25@mail.ru;
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Publication History

Received 15 June 2005
Publication Date:
11 January 2006 (online)

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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

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6

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