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Synthesis 2017; 49(09): 1905-1930
DOI: 10.1055/s-0036-1589483
DOI: 10.1055/s-0036-1589483
review
Copper-Catalyzed Arylation with Diaryliodonium Salts
Further Information
Publication History
Received: 01 December 2016
Accepted after revision: 06 January 2017
Publication Date:
06 March 2017 (online)
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
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