Journal
SCIENCE
Volume 357, Issue 6348, Pages -Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aan3679
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Funding
- Marie Sklodowska-Curie Fellowship [EMTECS/652890]
- European Research Council [670668]
- UK Engineering and Physical Sciences Research Council [EP/I038071/1]
- Engineering and Physical Sciences Research Council [EP/I038071/1, EP/K03927X/1] Funding Source: researchfish
- EPSRC [EP/K03927X/1, EP/I038071/1] Funding Source: UKRI
- European Research Council (ERC) [670668] Funding Source: European Research Council (ERC)
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The conversion of widely available carboxylic acids into versatile boronic esters would be highly enabling for synthesis. We found that this transformation can be effected by illuminating the N-hydroxyphthalimide ester derivative of the carboxylic acid under visible light at room temperature in the presence of the diboron reagent bis(catecholato)diboron. A simple workup allows isolation of the pinacol boronic ester. Experimental evidence suggests that boryl radical intermediates are involved in the process. The methodology is illustrated by the transformation of primary, secondary, and tertiary alkyl carboxylic acids as well as a diverse range of natural-product carboxylic acids, thereby demonstrating its broad utility and functional group tolerance.
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