Supramolecular Reactor in an Aqueous Environment:  Aromatic Cross Suzuki Coupling Reaction at Room Temperature

We have investigated supramolecular reactors for the Suzuki coupling reactions of aryl halides with phenyl boronic acids by using self-assembly of amphiphilic rod−coil molecules in aqueous solution at room temperature. All the rod−coil molecules synthesized in this work showed to self-assemble into...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 70; no. 22; pp. 8956 - 8962
Main Authors Ryu, Ja-Hyoung, Jang, Cheong-Jin, Yoo, Yong-Sik, Lim, Sung-Gon, Lee, Myongsoo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.10.2005
Amer Chemical Soc
Subjects
Anisoles - chemistry
Boronic Acids - chemistry
Bromus - chemistry
Catalysis
Chemistry
Chemistry, Organic
Exact sciences and technology
Models, Chemical
Molecular Structure
Noncondensed benzenic compounds
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Spectrum Analysis
Temperature
Water - chemistry
ORGANIZATION
COLUMNAR
ROD-COIL MOLECULES
COPOLYMER
Encapsulation
Self assembly
Chemical solution
Haloarene
Micelle
Amphiphilic compound
Chemical coupling
Suzuki coupling
Biphenyl derivatives
Aqueous medium
Supramolecular structure
Boron Organic compounds
Aromatic compound
Hydrophilic compound
Aqueous solution
Reactor
Chemical synthesis
Boronic acids
Comparative study
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Summary:We have investigated supramolecular reactors for the Suzuki coupling reactions of aryl halides with phenyl boronic acids by using self-assembly of amphiphilic rod−coil molecules in aqueous solution at room temperature. All the rod−coil molecules synthesized in this work showed to self-assemble into discrete micelles consisting of aromatic rod bundles encapsulated by hydrophilic poly(ethylene oxide) coils. We present a comparative study of rod−coil molecules' efficiency as supramolecular reactors for Suzuki coupling reaction. The closed-packed aromatic bundles play an efficient role in supramolecular reactors for the coupling reactions at room temperature. The supramolecular reactor based on hexa-p-phenylene confers unprecedented activity, allowing reactions to be performed at very low catalyst levels, without conventional heating or microwave.
Bibliography:istex:415464417AF0ED2805B04510CB25266D63972674
ark:/67375/TPS-NP5JTS4W-P
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SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo051398q