An efficient palladium(II)-catalyzed intermolecular direct ortho-alkenylation and acetoxylation of phenols has been developed. The reaction proceeded via a seven-membered cyclopalladated intermediate and showed complete regio- and diastereoselectivity. The approach also provided an efficient route for the synthesis of coumarins and benzofurans.
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http://dx.doi.org/10.1002/asia.201601413 | DOI Listing |
Org Lett
December 2024
Division of Medicinal Chemistry, CSIR-Institute of Microbial Technology, Chandigarh 160036, India.
A novel palladium-catalyzed intramolecular C-H amination via oxidative coupling exploiting inactivated N-substituted aryl amines on indoles for the one-pot synthesis of novel 11-benzo[4,5]imidazo[1,2-]indole derivatives is reported. The optimized reaction conditions accommodated a wide range of electronic variations on both the indole and the pendant aryl amine ring, resulting in products with good to excellent yields.
View Article and Find Full Text PDFJ Org Chem
December 2024
Jiangsu Key Laboratory for Chemistry of Low Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300, China.
An unprecedented Pd-catalyzed cascade alkyne insertion/Heck/C-H activation reaction of -iodophenyl alkenyl ethers and diarylacetylenes has been developed. Diversified tetracyclic-fused dihydroindeno[2,1-]chromenes bearing a quaternary center were constructed in an efficient, straightforward, and atom-economic way with good to excellent yields. The protocol features high bonding efficiency, operational simplicity, broad substrate scope, and easy scale-up.
View Article and Find Full Text PDFChem Commun (Camb)
December 2024
Department of Chemistry, School of Pharmacy, Air Force Medical University, Xi'an, 710032, China.
An efficient synthesis of continuously substituted quinoline derivatives palladium-catalyzed intramolecular 6- imidoylative cyclization of -alkenyl aryl isocyanides with (hetero)aryl halides or vinylic triflates has been developed. The reaction proceeds through the concerted metalation-deprotonation (CMD) mechanism by activation of a vinyl C-H bond with imidoylpalladium assisted by the carboxylate.
View Article and Find Full Text PDFOrg Lett
December 2024
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China.
Palladium-mediated, ligand-promoted C-H fluorinated olefination of aromatic derivatives is reported employing 2-bromo-3,3,3-trifluoropropene (BTP) as the fluorinating reagent. Bioactive compounds, such as Isatin, exhibited excellent compatibility with this reaction, underscoring the significance of this methodology for the synthesis of important derivatives.
View Article and Find Full Text PDFChem Sci
December 2024
Centre for Membrane Separations, Adsorption, Catalysis and Spectroscopy for Sustainable Solutions (cMACS), KU Leuven 3001 Leuven Belgium
Palladium(ii)-catalyzed dehydrogenative coupling of aliphatic olefins would enable an efficient route to (conjugated) dienes, but remains scarcely investigated. Here, 2-hydroxypyridine (2-OH-pyridine) was found to be an effective ligand for Pd(ii) in the activation of vinylic C(sp)-H bonds. While reoxidation of Pd(0) is challenging in many catalytic oxidations, one can avoid in this reaction that the reoxidation becomes rate-limiting, even under ambient O pressure, by working in coordinating solvents.
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