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

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
Further Information

Publication History

Received: 08 January 2015

Accepted: 17 February 2015

Publication Date:
26 March 2015 (online)

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

 
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