Copper-Catalyzed Arylation with Diaryliodonium Salts

Dedicated to the memory of Prof. José Barluenga

Abstract

The unique reactivity of diaryliodonium salts with copper complexes has been applied to a variety of synthetic organic transformations. These hypervalent iodine compounds have been used for diverse copper-catalyzed cross-coupling reactions including C–H functionalizations, enantioselective C–C bond formation, cascade reactions and different heteroatom arylation processes. This review provides a summary of recent developments on this topic and discusses both the synthetic utility and mechanisms of these transformations.

1 Introduction

2 Historical Background

3 Arylation of Carbon Nucleophiles

3.1 Arylation of Organometallic Compounds

3.2 Arylation of Heteroarenes

3.3 Arylation of Arenes

3.4 Arylation of Alkenes

3.5 Arylation of Alkynes

4 Nitrogen Arylation

4.1 Arylation of Acyclic Amine Derivatives

4.2 Arylation of Cyclic Amine Derivatives

4.3 Arylation of Nitriles

4.4 Arylation of Azides

5 Oxygen Arylation

6 Arylation of Other Heteroatoms

6.1 Fluorine Arylation

6.2 Sulfur Arylation

6.3 Phosphorus Arylation

6.4 Iodine Arylation

7 Summary and Conclusions

Key words

copper - iodine - hypervalent compounds - catalysis - arylation

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