Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes to Generate Dialkyl Ketones

Jesus I. Martinez Alvarado, Alyssa B. Ertel, Andrea Stegner, Erin E. Stache, Abigail G. Doyle

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

A general protocol for the hydroacylation of styrenes from aliphatic carboxylic acids is reported. These reactions proceed via β-scission of a phosphoranyl radical that is accessed by photoredox catalysis, followed by addition of the resulting acyl radical to the styrenyl olefin. We show that phosphine tunability is critical for efficient intermolecular coupling due to competitive quenching of the photocatalyst by the olefin. Primary, secondary, and structurally rigid tertiary carboxylic acids all generate valuable unsymmetrical dialkyl ketones.

Original languageEnglish (US)
Pages (from-to)9940-9944
Number of pages5
JournalOrganic letters
Volume21
Issue number24
DOIs
StatePublished - Dec 20 2019

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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