Mechanistic chemical investigation demonstrates stereoselective secondary functionalization of 1,2-bis-boronic esters, highlighting alkoxide-assisted photoredox radical control.
Site-specific functionalization of the secondary C–B bond of 1,2-bis-boronic esters has been proven to be an important method for the generation of 1,2-bis-functionalized compounds in a highly stereoselective manner. We have explored previously unknown secondary selective alkenylation, allylation, alkynylation and addition to aryl vinyl trifluoromethane, which proceeds via a novel reaction mechanism: alkoxide-mediated photoredox activation to generate secondary radicals over the primary one.
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Mahato et al. (2024) studied this question.
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