Reductive Arylation of Arylidene Malonates Using Photoredox Catalysis

Rick C. Betori, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

A strategy with arylidene malonates provides access to β-umpolung single-electron species. Reported here is the utilization of these operators in intermolecular radical-radical arylations, while avoiding conjugate addition/dimerization reactivity that is commonly encountered in enone-based photoredox chemistry. This reactivity relies on tertiary amines that serve to both activate the arylidene malonate for single-electron reduction by a proton-coupled electron transfer mechanism as well as serve as a terminal reductant. This photoredox catalysis pathway demonstrates the versatility of stabilized radicals for unique bond-forming reactions.

Original languageEnglish (US)
Pages (from-to)10350-10357
Number of pages8
JournalACS Catalysis
Volume9
Issue number11
DOIs
StatePublished - Nov 1 2019

Keywords

  • arylation
  • arylidene malonates
  • photoredox catalysis
  • proton coupled electron transfer
  • β-umpolung

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Reductive Arylation of Arylidene Malonates Using Photoredox Catalysis'. Together they form a unique fingerprint.

Cite this