Direct deoxygenative borylation of carboxylic acids

Jianbin Li, Chia-Yu Huang, Mohamad Ataya, Rustam Z. Khaliullin () and Chao-Jun Li ()
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Jianbin Li: McGill University
Chia-Yu Huang: McGill University
Mohamad Ataya: McGill University
Rustam Z. Khaliullin: McGill University
Chao-Jun Li: McGill University

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract Carboxylic acids are readily available, structurally diverse and shelf-stable; therefore, converting them to the isoelectronic boronic acids, which play pivotal roles in different settings, would be highly enabling. In contrast to the well-recognised decarboxylative borylation, the chemical space of carboxylic-to-boronic acid transformation via deoxygenation remains underexplored due to the thermodynamic and kinetic inertness of carboxylic C-O bonds. Herein, we report a deoxygenative borylation reaction of free carboxylic acids or their sodium salts to synthesise alkylboronates under metal-free conditions. Promoted by a uniquely Lewis acidic and strongly reducing diboron reagent, bis(catecholato)diboron (B2cat2), a library of aromatic carboxylic acids are converted to the benzylboronates. By leveraging the same borylative manifold, a facile triboration process with aliphatic carboxylic acids is also realised, diversifying the pool of available 1,1,2-alkyl(trisboronates) that were otherwise difficult to access. Detailed mechanistic studies reveal a stepwise C-O cleavage profile, which could inspire and encourage future endeavours on more appealing reductive functionalisation of oxygenated feedstocks.

Date: 2021
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DOI: 10.1038/s41467-021-25229-8

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