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Reversible Click Reactions with Boronic Acids to Build Supramolecular Architectures in Water
Author(s) -
Arzt Matthias,
Seidler Christiane,
Ng David Y. W.,
Weil Tanja
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201402061
Subject(s) - phenylboronic acid , bioorthogonal chemistry , boronic acid , supramolecular chemistry , chemistry , bifunctional , combinatorial chemistry , click chemistry , hydrolysis , reagent , organic chemistry , catalysis , molecule
The interaction of boronic acids with various bifunctional reagents offers great potential for the preparation of responsive supramolecular architectures. Boronic acids react with 1,2‐diols yielding cyclic boronate esters that are stable at pH>7.4 but can be hydrolyzed at pH<5.0. The phenylboronic acid (PBA)–salicylhydroxamic acid (SHA) system offers ultra‐fast reaction kinetics and high binding affinities. This Focus Review summarizes the current advances in exploiting the bioorthogonal interaction of boronic acids to build pH‐responsive supramolecular architectures in water.