Direct Synthesis of 2-Hydroxytrifluoroethylacetophenones via Organophotoredox-Mediated Net-Neutral Radical/Polar Crossover

Albert Gallego-Gamo, Pau Sarró, Yingmin Ji, Roser Pleixats i Rovira, Elies Molins, Carolina Gimbert Suriñach, Adelina Vallribera Massó, Albert Granados Toda

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1 Citation (Scopus)

Abstract

Alkene difunctionalization is a very attractive tool in synthetic organic chemistry. Herein, we disclose an operationally and practically simple method to access 2-hydroxytrifluoroethylacetophenones from styrene derivatives via photoredox catalysis. This light-mediated transformation promotes the generation of the 1-hydroxy-2,2,2-trifluoroethyl carbon-centered radical as key synthon, which undergoes Giese addition with styrenes followed by a Kornblum oxidation process. The presented method is not only mild and cost-effective, but also utilizes an organic photocatalyst and DMSO as oxidant. Experimental investigations support the operative mechanism via net-neutral radical/polar crossover.
Original languageEnglish
Pages (from-to)11682-11692
Number of pages11
JournalJournal of Organic Chemistry
Volume89
Issue number16
DOIs
Publication statusPublished - 1 Aug 2024

Keywords

  • Alkenes
  • Catalysis
  • Difunctionalization
  • Trifluoromethyl ketones

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