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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Review Article

Palladium-Catalysed Intermolecular Direct C–H Bond Arylation of Heteroarenes with Reagents Alternative to Aryl Halides: Current State of the Art

Author(s): Renzo Rossi* and Maurizio Ciofalo*

Volume 26, Issue 3, 2022

Published on: 01 February, 2022

Page: [215 - 274] Pages: 60

DOI: 10.2174/1385272826666220201124008

Price: $65

Abstract

This unprecedented review with 322 references provides a critical up-to-date picture of the Pd-catalysed intermolecular direct C–H bond arylation of heteroarenes with arylating reagents alternative to aryl halides that include aryl sulfonates (aryl triflates, tosylates, mesylates, and imidazole- 1-sulfonates), diaryliodonium salts, [(diacetoxy)iodo]arenes, arenediazonium salts, 1-aryltriazenes, arylhydrazines and N’-arylhydrazides, arenesulfonyl chlorides, sodium arenesulfinates, arenesulfinic acids, and arenesulfonohydrazides. Particular attention has been paid to summarise the preparation of the various arylating reagents and to highlight the practicality, versatility, and limitations of the various developed arylation protocols, also comparing their results with those achieved in analogous Pd-catalysed arylation reactions involving the use of aryl halides as electrophiles. Mechanistic proposals have also been briefly summarised and discussed. However, data concerning Pd-catalysed direct C–H bond arylations involving the C–H bonds of aryl substituents of the examined heteroarene derivatives have not been taken into account.

Keywords: Heteroarenes, palladium, direct C–H bond arylation, catalysis, regioselectivity, aryl halides.

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