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

Adam Noble, Riccardo S. Mega, Daniel Pflästerer, Eddie L. Myers, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

50 Citations (Scopus)
436 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)2155-2159
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number8
Early online date26 Jan 2018
DOIs
Publication statusPublished - 19 Feb 2018

Keywords

  • Amino acids
  • Boron
  • Photochemistry
  • Radical reactions
  • Reaction mechanisms

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