Synthesis, Characterization, and Applications of Zwitterions Containing a Carbanion Moiety

A trifle of triflyl: N‐substituted anilines react with 1,1,3,3‐tetrakis(triflyl)propane to give a 2,2‐bis(triflyl)ethyl group at the para position of the ring. The product is a zwitterion with a carbanion and an ammonium moiety, and can be used as an acid catalyst for organic reactions (see scheme)....

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Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 52; no. 5; pp. 1560 - 1563
Main Authors Yanai, Hikaru, Yoshino, Tasuku, Fujita, Masaya, Fukaya, Haruhiko, Kotani, Akira, Kusu, Fumiyo, Taguchi, Takeo
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 28.01.2013
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
aldol reaction
Aniline
Anions - chemistry
carbanions
Carbon - chemistry
Catalysts
Chemistry
Chemistry, Multidisciplinary
Crystallography, X-Ray
homogeneous catalysis
Molecular Conformation
Physical Sciences
Quaternary Ammonium Compounds - chemistry
Rings (mathematics)
Science & Technology
Synthesis
synthetic methodology
zwitterions
aldol reaction
METHIDE
ACIDITIES
carbanions
ACIDS
ESTERIFICATION
MUKAIYAMA-MICHAEL REACTION
TRANSESTERIFICATION
EFFICIENT CATALYST
homogeneous catalysis
X-RAY
zwitterions
synthetic methodology
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Summary:A trifle of triflyl: N‐substituted anilines react with 1,1,3,3‐tetrakis(triflyl)propane to give a 2,2‐bis(triflyl)ethyl group at the para position of the ring. The product is a zwitterion with a carbanion and an ammonium moiety, and can be used as an acid catalyst for organic reactions (see scheme).
Bibliography:MEXT
ArticleID:ANIE201208809
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istex:58D1AE4AA293657493BB398942DBEBD06E5F57AF
Tf2CH2 was kindly provided by the Central Glass Co., Ltd. This work was partially supported by a Grant-in-Aid for Scientific Research on Innovative Areas "Advanced Molecular Transformations by Organocatalysts" from the MEXT. We also thank the Asahi Glass Foundation.
was kindly provided by the Central Glass Co., Ltd. This work was partially supported by a Grant‐in‐Aid for Scientific Research on Innovative Areas “Advanced Molecular Transformations by Organocatalysts” from the MEXT. We also thank the Asahi Glass Foundation.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201208809