Supramolecular reactor in an aqueous environment: aromatic cross Suzuki coupling reaction at room temperature.
[reaction: see text] 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.
Ryu
Ja-Hyoung
JH
Center for Supramolecular Nano-Assembly and Department of Chemistry, Yonsei University, Seoul, Korea.
Jang
Cheong-Jin
CJ
Yoo
Yong-Sik
YS
Lim
Sung-Gon
SG
Lee
Myongsoo
M
D000840:Anisoles / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry; D031724:Bromus / Q000737:chemistry; D002384:Catalysis; D008956:Models, Chemical; D015394:Molecular Structure; D013057:Spectrum Analysis; D013696:Temperature; D014867:Water / Q000737:chemistry*
D000840:Anisoles; D001897:Boronic Acids; D014867:Water; C060998:anisole; C010686:benzeneboronic acid