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

Authors :
Eddie L. Myers
Riccardo S. Mega
Adam Noble
Varinder K. Aggarwal
Daniel Pflästerer
Source :
Angewandte Chemie International Edition, Angewandte Chemie (International Ed. in English), Noble, A, Mega, R S, Pflästerer, D, Myers, E L & Aggarwal, V K 2018, ' Visible-Light-Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters : Rapid Access to γ-Amino Boronic Esters ', Angewandte Chemie-International Edition, vol. 57, no. 8, pp. 2155-2159 . https://doi.org/10.1002/anie.201712186
Publication Year :
2018

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 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 of potential biological importance.

Details

ISSN :
14337851
Database :
OpenAIRE
Journal :
Angewandte Chemie International Edition
Accession number :
edsair.doi.dedup.....2e097e3df6b2725cff06fee7b6bcf079
Full Text :
https://doi.org/10.1002/anie.201712186