Decarboxylative Conjunctive Cross-coupling of Vinyl Boronic Esters using Metallaphotoredox Catalysis

Riccardo S. Mega, Vincent K. Duong, Adam Noble*, Varinder Kumar Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

12 Citations (Scopus)

Abstract

The synthesis of complex alkyl boronic esters via a conjunctive cross‐coupling of vinyl boronic esters with carboxylic acids and aryl iodides is described. The reaction proceeds under mild metallaphotoredox conditions and involves an unprecedented decarboxylative radical addition/cross‐coupling cascade of vinyl boronic esters. Excellent functional group tolerance is displayed, and application of a range of carboxylic acids, namely secondary α‐amino acids, and aryl iodides provides efficient access to highly functionalized alkyl boronic esters. The decarboxylative conjunctive cross‐coupling was also applied to the synthesis of sedum alkaloids.
Original languageEnglish
Pages (from-to)4375-4379
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number11
Early online date3 Feb 2020
DOIs
Publication statusPublished - 9 Mar 2020

Keywords

  • metallaphotoredox catalysis
  • decarboxylative crosscoupling
  • conjunctive cross-coupling
  • alkyl boronic esters
  • carboxylic acids

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