Abstract

A simple and general method for arylation of carbon-hydrogen bonds in compounds containing directing groups has been developed. Anilides, benzylamines, benzoic acids, 2-aryl and alkyl­pyridines can be arylated in ortho-positions by using a combination of substrate, aryl iodide, silver acetate and catalytic palladium acetate. The use of a pyridine-containing removable auxiliary ligand ­allows the arylation of β-positions in carboxylic acid derivatives and γ-positions in amine derivatives. Non-activated sp3 carbon-hydrogen bonds are also reactive. A mechanistically distinct method for the alkenylation of anilides has also been developed.

Keywords

ChemistryRegioselectivityArylAlkylAmine gas treatingPalladiumCatalysisHydrogen bondLigand (biochemistry)PyridineOrganic chemistryIodideBenzoic acidSurface modificationSubstrate (aquarium)Combinatorial chemistryMedicinal chemistryMolecule

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Publication Info

Year
2006
Type
article
Volume
2006
Issue
20
Pages
3382-3388
Citations
243
Access
Closed

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Cite This

Olafs Daugulis, V. G. Zaitsev, Dmitry Shabashov et al. (2006). Regioselective Functionalization of Unreactive Carbon-Hydrogen Bonds. Synlett , 2006 (20) , 3382-3388. https://doi.org/10.1055/s-2006-956468

Identifiers

DOI
10.1055/s-2006-956468