A VERSATILE SYNTHESIS OF ARYLACETONES FROM ARYL HALIDES AND ACETYLACETONATE
Reaction of aryl halides with sodium or potassium acetylacetonate in the presence of a copper catalyst affords directly arylacetones resulted from deacetylation of initially formed 3-arylacetylacetones in good yields.
Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source
Methylation of organohalides represents a valuable transformation, but typically requires harsh reaction conditions or reagents. We report a radical approach for the methylation of (hetero)aryl chlorides using nickel/photoredox catalysis wherein trimethyl orthoformate, a common laboratory solvent, serves as a methyl source. This method permits methylation of (hetero)aryl chlorides and acyl chlorides at an early and late stage with broad functional group compatibility. Mechanistic investigations indicate that trimethyl orthoformate serves as a source of methyl radical via β-scission from a tertiary radical generated upon chlorine-mediated hydrogen atom transfer.
Kariofillis, Stavros K.,Shields, Benjamin J.,Tekle-Smith, Makeda A.,Zacuto, Michael J.,Doyle, Abigail G.
supporting information
p. 7683 - 7689
(2020/04/22)
Alternative synthesis of 2-arylpropanoic acids from enolate and aryl halides
Arylpropanoic acids, a type of non-steroidal antiinflammatory drug, have been prepared in liquid ammonia by photo-radical nucleophilic substitution of halogenoarenes with sodium N,N-dimethylacetamide enolate followed by methylation and hydrolysis.Rapid substitution occured in many cases with good to excellent yields of arylpropanoic acids.The title compounds have also been prepared by arylation of sodium acetone enolate with methylation and oxidation in a haloform reaction.
Ferrayoli, Carlos G.,Palacios, Sara M.,Alonso, Ruben A.
p. 1635 - 1638
(2007/10/02)
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