Synthesis 2018; 50(11): 2150-2162
DOI: 10.1055/s-0037-1609715
short review
© Georg Thieme Verlag Stuttgart · New York

Metal-Catalyzed Oxidative Coupling of Ketones and Ketone Enolates

Sandip Murarka*
a   Department of Chemistry, Indian Institute of Technology Jodhpur, NH-65, Nagaur Road, Karwar-342037, Jodhpur District, Rajasthan, India   Email: sandipmurarka@iitj.ac.in
,
Andrey P. Antonchick*
b   Abteilung für Chemische Biologie, Max-Planck-Institut für Molekulare Physiologie, Otto-Hahn-Straße 11, 44227 Dortmund, Germany   Email: andrey.antonchick@mpi-dortmund.mpg.de
c   Fakultät Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Straße 4a, 44227 Dortmund, Germany
› Author Affiliations
A.P.A. acknowledges the support of DFG (Heisenberg scholarship AN 1064/4-1) and Boehringer Ingelheim Foundation (Plus 3).
Further Information

Publication History

Received: 25 February 2018

Accepted after revision: 21 March 2018

Publication Date:
03 May 2018 (online)


Abstract

Recent years have witnessed a significant advancement in the field of radical oxidative coupling of ketones towards the synthesis of highly useful synthetic building blocks, such as 1,4-dicarbonyl compounds, and biologically important heterocyclic and carbocyclic compounds. Besides oxidative homo- and cross-coupling of enolates, other powerful methods involving direct C(sp3)–H functionalizations of ketones­ have emerged towards the synthesis of 1,4-dicarbonyl compounds. Moreover, direct α-C–H functionalization of ketones has also allowed an efficient access to carbocycles and heterocycles. This review summarizes all these developments made since 2008 in the field of metal-catalyzed/promoted radical-mediated functionalization of ketones at the α-position.

1 Introduction

2 Synthesis of 1,4-Dicarbonyl Compounds

3 Synthesis of Heterocyclic Scaffolds

4 Synthesis of Carbocyclic Scaffolds

5 Conclusion