%0 Journal Article
%T Difluorocarbene-Promoted O-O Bond Activation of Peroxy Acids for Electrophilic Carboxylation of Boronic Acids.
%A Niu HL
%A Luo PX
%A Zhang SL
%J Chem Asian J
%V 0
%N 0
%D 2024 Jul 17
%M 39018086
%F 4.839
%R 10.1002/asia.202400613
%X In this study, a difluorocarbene-promoted O-O bond activation of peroxy acids is developed through the insertion of difluorocarbene into O-H bond. This activation strategy in synergy with O-B coordination with boronic acids/ester greatly polarizes the O-O bond for in-situ generation of carboxylium species that reacts with the nucleophilic part of boronic acids in a concerted way to produce esters. Good efficiency and functional group tolerance are demonstrated. Application of this method to the functionalization of a boronic acid drug used as HSL enzyme inhibitor produces smoothly the ester derivative. This difluorocarbene-mediated O-O bond activation strategy is conceptually different from traditional radical type methods, and is also complementary to conventional esterification methods with a distinct retro-synthetic disconnection.