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Establishment of Broadly Applicable Reaction Conditions for the Palladium-Catalyzed Direct Arylation of Heteroatom-Containing Aromatic Compounds
The Journal of Organic Chemistry · 2009 · Vol. 74(5) · pp. 1826–1834
Benoît Liégault✉(University of Ottawa)David Lapointe(University of Ottawa)Laurence Caron(University of Ottawa)Anna Vlassova(University of Ottawa)Keith Fagnou(University of Ottawa)
Abstract
Conditions for the palladium-catalyzed direct arylation of a wide range of heterocycles with aryl bromides are reported. Those conditions employ a stoichiometric ratio of both coupling partners, as well as a substoichiometric quantity of pivalic acid, which results in significantly faster reactions. An evaluation of the influence of the nature of the aryl halide has also been carried out.
Catalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical ReactionsChemistryPalladiumPivalic acidArylHeteroatomCatalysisStoichiometryHalideReaction conditionsOrganic chemistry
MeSH terms
CatalysisHeterocyclic CompoundsHydrocarbons, BrominatedPalladiumStereoisomerismMolecular Structure
Funding
- Amgen
Citations
590
FWCI
35.89
field-weighted impact
References
124
Percentile
100%
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Cited by
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References
Air-Stable Trialkylphosphonium Salts: Simple, Practical, and Versatile Replacements for Air-Sensitive Trialkylphosphines. Applications in Stoichiometric and Catalytic Processes
Organic Letters · 2001 · 596 citations
Assisted Ruthenium-Catalyzed C−H Bond Activation: Carboxylic Acids as Cocatalysts for Generally Applicable Direct Arylations in Apolar Solvents
Organic Letters · 2008 · 391 citations
Copper-Catalyzed “Click” Reaction/Direct Arylation Sequence: Modular Syntheses of 1,2,3-Triazoles
Organic Letters · 2008 · 344 citations
Catalytic Functionalization of Arenes and Alkanes via C−H Bond Activation
Accounts of Chemical Research · 2001 · 1,388 citations
Palladium-Catalyzed Arylation of Electron-Rich Heterocycles with Aryl Chlorides
Organic Letters · 2007 · 387 citations
Palladium-Catalyzed Arylation of Azole Compounds with Aryl Halides in the Presence of Alkali Metal Carbonates and the Use of Copper Iodide in the Reaction
Bulletin of the Chemical Society of Japan · 1998 · 465 citations
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