Significant enhancement in the efficiency and selectivity of iron-catalyzed oxidative cross-coupling of phenols by fluoroalcohols

Eden Gaster, Yulia Vainer, Almog Regev, Sachin Narute, Kavitha Sudheendran, Aviya Werbeloff, Hadas Shalit, Doron Pappo

Research output: Contribution to journalArticlepeer-review

93 Scopus citations

Abstract

Significant enhancement of both the rate and the chemoselectivity of iron-catalyzed oxidative coupling of phenols can be achieved in fluorinated solvents, such as 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), 2,2,2-trifluoroethanol (TFE), and 1-phenyl-2,2,2-trifluoroethanol. The generality of this effect was examined for the cross-coupling of phenols with arenes and polycyclic aromatic hydrocarbons (PAHs) and of phenol with β-dicarbonyl compounds. The new conditions were utilized in the synthesis of 2-dehydroxycalodenin B in only four synthetic steps. Not just a solvent: The use of fluorinated solvents leads to a significant rate acceleration and enhancement of the chemoselectivity of the iron-catalyzed oxidative coupling of phenols. This method was used for the synthesis of 2-dehydroxycalodenin B.

Original languageEnglish
Pages (from-to)4198-4202
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number14
DOIs
StatePublished - 27 Mar 2015

Keywords

  • cross-dehydrogenative coupling
  • fluorinated solvents
  • iron catalysis
  • oxidative cross-coupling
  • phenols

Fingerprint

Dive into the research topics of 'Significant enhancement in the efficiency and selectivity of iron-catalyzed oxidative cross-coupling of phenols by fluoroalcohols'. Together they form a unique fingerprint.

Cite this