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

Almog Regev; Hadas Shalit; Doron Pappo

doi:10.1055/s-0034-1380360

Synthesis, Table of Contents

Synthesis 2015; 47(12): 1716-1725
DOI: 10.1055/s-0034-1380360

paper

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

Almog Regev

Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva 84105, Israel Email: pappod@bgu.ac.il

,

Hadas Shalit

Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva 84105, Israel Email: pappod@bgu.ac.il

,

Doron Pappo*

Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva 84105, Israel Email: pappod@bgu.ac.il

› Author Affiliations

Abstract

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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.

Key words

iron - catalysis - cross-coupling - phenols - ketones - esters

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References

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