Hydrogen peroxide-responsive triggers based on borinic acids: molecular insights into the control of oxidative rearrangement
Résumé
Arylborinic acids represent new, efficient, and underexplored hydrogen peroxide-responsive triggers. In contrast to boronic acids, two concomitant oxidative rearrangements are involved in the complete oxidation of these species, which might represent a major limitation for an efficient effector (drug or fluorophore) release. Herein, we describe a comprehensive study of H2O2-mediated unsymmetrical arylborinic acid oxidation to investigate the factors that could selectively guide their oxidative rearrangement. The o-CF3 substituent was found to be an excellent directing group since complete regioselectivity was obtained on borinic acid models. This result was successfully applied to synthesizing new borinic acid-based fluorogenic probes, which exclusively release the fluorescent moiety upon H2O2 treatment. These compounds maintained their superior kinetic properties compared to boronic acids, thus further enhancing the potential of arylborinic acids as valuable new H2O2-sensitive triggers.
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Chimie
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