Thieme E-Journals - Synthesis / Abstract
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Synthesis 2015; 47(12): 1716-1725
DOI: 10.1055/s-0034-1380360
paper
© Georg Thieme Verlag Stuttgart · New York

Iron-Catalyzed Oxidative C–C and C–O Coupling of Halophenols to α-Substituted β-Keto Esters

Authors

  • Almog Regev

    Department of Chemistry, Ben-Gurion University of the Negev,
    Beer-Sheva 84105,
    Israel   
  • Hadas Shalit

    Department of Chemistry, Ben-Gurion University of the Negev,
    Beer-Sheva 84105,
    Israel   
  • Doron Pappo*

    Department of Chemistry, Ben-Gurion University of the Negev,
    Beer-Sheva 84105,
    Israel   


Graphical Abstract

Abstract

The iron-catalyzed oxidative cross-coupling of halophenols to α-substituted β-keto esters takes place through one of two modes: oxidative C–C coupling or oxidative C–O coupling. A mechanistic investigation revealed that the chemoselectivity of these reactions is determined by the electronic and steric properties of the two coupling partners.

Supporting Information