[reaction: see text] A palladium-catalyzed arylation of allylic acetates followed by beta-acetoxy elimination was shown to produce Heck-type coupling products. Optimal reaction conditions employed ligand-free palladium on carbon in the presence of tetrabutylammonium chloride, a trialkylamine base, and water.
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http://dx.doi.org/10.1021/ol051947e | DOI Listing |
J Org Chem
December 2024
Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam-Golm, Germany.
The synthesis of coumarin- and flavonoid-chalcone hybrids via Pd-catalyzed Heck-type coupling of arene diazonium salts and 8-allylcoumarins and -flavonoids is reported. The β-hydride elimination step proceeds with high regioselectivity if an OMOM-substituent is present at the position C7, adjacent to the allyl group. A selective allylic oxidation of the coupling products was accomplished using DDQ in the presence of silica to furnish the chalcones.
View Article and Find Full Text PDFChemistry
November 2024
University of Sussex, Chemistry, Chichester III, Falmer Campus, Brighton, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
RSC Adv
August 2024
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University Suzhou 215123 P. R. China
The copper-catalyzed strategy employing the 8-aminoquinoline directing group has proven to be a highly advantageous approach for functionalizing C-H bonds. In this study, we present the successful application of this strategy to accomplish Heck-type coupling reactions and construct β-lactam skeletons, simultaneously introducing a unique cyano functional group. The resulting Heck-type coupling products demonstrate good stereo- and region-selectivity.
View Article and Find Full Text PDFOrg Biomol Chem
August 2024
Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
An efficient synthesis of aryl enopyranones an oxidative Heck-type coupling reaction between ether protected D/L-glycals and different aryl halides is developed. This one-step method attaches an aryl group at the C-1 position keeping the C-1/C-2 double bond intact the Saegusa-Ito type oxidation, thus facilitating the synthesis of medicinally important 2-deoxy-β-aryl-C-glycosides after Pd/C reduction.
View Article and Find Full Text PDFAcc Chem Res
June 2024
Department of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo 162-0041, Japan.
ConspectusAromatic esters are cost-effective, versatile, and commonly used scaffolds that are readily synthesized or encountered as synthetic intermediates. While most conventional reactions involving these esters are nucleophilic acyl substitutions or 1,2-nucleophilic additions─where a nucleophile attacks the carbonyl group, decarbonylative transformations offer an alternative pathway by using the carbonyl group as a leaving group. This transition-metal-catalyzed process typically begins with oxidative addition of the C(acyl)-O bond to the metal.
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