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Visible-Light-Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to ?-Amino Boronic Esters.

ABSTRACT: The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single-electron reduction of an ?-boryl radical intermediate to the corresponding anion. The reaction is amenable to a diverse range of substrates, including ?-amino, ?-oxy, and alkyl carboxylic acids, thus providing a novel method to rapidly access boron-containing molecules of potential biological importance.

SUBMITTER: Noble A

PROVIDER: S-EPMC5838549 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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Visible-Light-Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ-Amino Boronic Esters.

Noble Adam A Mega Riccardo S RS Pflästerer Daniel D Myers Eddie L EL Aggarwal Varinder K VK

Angewandte Chemie (International ed. in English) 20180126 8

The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single-electron reduction of an α-boryl radical intermediate to the corresponding anion. The reaction is amenable to a diverse range of substrates, including α-amino, α-oxy, and alkyl carboxylic acids, thus providing a novel method to rapidly access boron-containing molecules ...[more]

PMID: 29316095

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