Search results for "heteroarenes"

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Palladium-Catalyzed Direct Arylation of Heteroaromatics with Activated Aryl Chlorides Using a Sterically Relieved Ferrocenyl-Diphosphane

2012

International audience; The palladium-catalyzed direct arylations at C3 or C4 positions of heteroaromatics are known to be more challenging than at C2 or C5 positions. Aryl chlorides are also challenging substrates for direct arylation of heteroaromatics. We observed that in the presence of a palladium-catalyst combining only 0.5 mol % of Pd(OAc)2 with the sterically relieved new ferrocenyl diphosphane Sylphos, the direct arylation at C3 or C4 of oxazoles, a benzofuran, an indole, and a pyrazole was found to proceed in moderate to high yields using a variety of electron deficient aryl chlorides. Turnover numbers up to 176 have been obtained with this catalyst. Assessment of the electron-don…

ligand designSteric effectsC−H bond functionalizationaryl chlorideschemistry.chemical_elementPyrazole010402 general chemistry01 natural sciencesMedicinal chemistryCatalysis[ CHIM.CATA ] Chemical Sciences/Catalysischemistry.chemical_compoundOrganic chemistryDiphosphaneMethyleneBenzofuranIndole test010405 organic chemistryArylferrocenylphosphaneheteroarenes[CHIM.CATA]Chemical Sciences/CatalysisGeneral Chemistrypalladium0104 chemical scienceschemistry13. Climate actionPalladiumACS Catalysis
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Palladium-Catalysed Intermolecular Direct C–H Bond Arylation of Heteroarenes with Reagents Alternative to Aryl Halides: Current State of the Art

2022

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 limit…

Organic ChemistryHeteroarenes palladium direct C–H bond arylation catalysis regioselectivity aryl halidesSettore CHIM/06 - Chimica OrganicaCurrent Organic Chemistry
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