Halogen-Bond-Induced Activation of a Carbon-Heteroatom Bond

Halogen-Bond-Induced Activation of a Carbon-Heteroatom Bond

I⋅⋅⋅Br‐idging: Benzhydryl bromide can be activated by novel halogen‐bond donors and subsequently undergoes a Ritter‐like reaction with acetonitrile (see scheme). Comparative experiments with non‐iodinated reference compounds and tests with added acids indicate that halogen bonds are very likely the...

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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 50; no. 31; pp. 7187 - 7191
Main Authors: Walter, Sebastian M., Kniep, Florian, Herdtweck, Eberhardt, Huber, Stefan M.
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 25-07-2011
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Edition:International ed. in English
Subjects:
alkylation
anions
halogen bonds
imidazolium salts
solvolysis
Online Access:Get full text
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Summary:I⋅⋅⋅Br‐idging: Benzhydryl bromide can be activated by novel halogen‐bond donors and subsequently undergoes a Ritter‐like reaction with acetonitrile (see scheme). Comparative experiments with non‐iodinated reference compounds and tests with added acids indicate that halogen bonds are very likely the basis for this effect. The activation seems to be applicable to other substrates as well.
Bibliography:Deutsche Forschungsgemeinschaft (DFG)
ArticleID:ANIE201101672
istex:7F27FA317026265F640056ED4EF4CA3C7C2BD5F0
Our research is funded by the Fonds der Chemischen Industrie (Liebig Scholarship to S.M.H.), the Deutsche Forschungsgemeinschaft (DFG), and the Leonhart-Lorenz-Foundation. S.M.W. thanks the TUM Graduate School. We thank Prof. Dr. Thorsten Bach and his group for their great support. We also thank the referees for helpful suggestions and comments.
Fonds der Chemischen Industrie
ark:/67375/WNG-5N88HXSQ-4
Leonhart-Lorenz-Foundation
These authors contributed equally to this work.
Our research is funded by the Fonds der Chemischen Industrie (Liebig Scholarship to S.M.H.), the Deutsche Forschungsgemeinschaft (DFG), and the Leonhart‐Lorenz‐Foundation. S.M.W. thanks the TUM Graduate School. We thank Prof. Dr. Thorsten Bach and his group for their great support. We also thank the referees for helpful suggestions and comments.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201101672