Synthesis 2019; 51(02): 334-358
DOI: 10.1055/s-0037-1609635
review
© Georg Thieme Verlag Stuttgart · New York

Cu(III)-Mediated Aerobic Oxidations

Kenneth Virgel N. Esguerra
a   Department of Chemistry, University of California–Berkeley, Berkeley, CA 94720, USA
,
b   Department of Chemistry, McGill University, 801 Sherbrooke St. W., Montreal, Quebec, H3A 0B8, Canada   Email: jean-philip.lumb@mcgill.ca
› Author Affiliations
Financial support was provided by the Natural Sciences and Engineering Council of Canada (NSERC, J.-P.L.). K.V.N.E acknowledges NSERC for a PDF scholarship.
Further Information

Publication History

Received: 19 August 2018

Accepted after revision: 07 October 2018

Publication Date:
03 December 2018 (online)


Abstract

CuIII species have been invoked in many copper-catalyzed transformations including cross-coupling reactions and oxidation reactions. In this review, we will discuss seminal discoveries that have advanced our understanding of the CuI/CuIII redox cycle in the context of C–C and C–heteroatom aerobic cross-coupling reactions, as well as C–H oxidation reactions mediated by CuIII–dioxygen adducts.

1 General Introduction

2 Early Examples of CuIII Complexes

3 Aerobic CuIII-Mediated Carbon–Heteroatom Bond-Forming Reactions

4 Aerobic CuIII-Mediated Carbon–Carbon Bond-Forming Reactions

5 Bioinorganic Studies of CuIII Complexes from CuI and O2

5.1 O2 Activation

5.2 Biomimetic CuIII Complexes from CuI and Dioxygen

5.2.1 Type-3 Copper Enzymes and Dinuclear Cu Model Complexes

5.2.2 Particulate Methane Monooxygenase and Di- and Trinuclear Cu Model Complexes

5.2.3 Dopamine–β-Monooxygenase and Mononuclear Cu Model Complexes

6 Conclusion