4-Aryl-2-quinolones from 3,3-Diarylacrylamides through Intramolecular Copper-Catalyzed C–H Functionalization/C–N Bond Formation

Free NH 3,3-diarylacrylamides are cyclized to substituted 2-quinolones in the presence of CuI, PPh₃, and KO-<i>t</i>-Bu in <i>o-</i>xylene at 100 °C. The reaction proceeds through a C–H functionalization/C–N bond formation process. With unsymmetrical 3,3-diarylacrylamides, high selectivity is observed using substrates where the aromatic ring <i>trans</i> to the amide group bears <i>o</i>-methyl, -chloro, or -bromo substituents

Palladium-Catalyzed Cascade Reactions of 1‑(3-Arylprop-2-ynyloxy)-2-bromo Benzene Derivatives with Organoboron Compounds

Applications of the cascade cyclocarbopalladation reaction followed by Suzuki–Miyaura coupling reactions of the readily available aryl-substituted propargylic aryl ethers with arylboronic acid and potassium <i>trans</i>-β-styryltrifluoroborate accomplish a new versatile entry in the synthesis of benzofuran derivatives. Notably, a new approach to the challenging synthesis of C3 functionalized 2-unsubstituted benzofurans has been developed by a cyclocarbopalladation/cross-coupling/aromatization process

Design, Palladium-Catalyzed Synthesis, and Biological Investigation of 2‑Substituted 3‑Aroylquinolin-4(1<i>H</i>)‑ones as Inhibitors of the Hedgehog Signaling Pathway

2-Substituted 3-aroylquinolin-4­(1<i>H</i>)-ones, prepared through a palladium-catalyzed carbonylative cyclization of <i>N</i>-(2-iodoaryl)­enaminones, proved to inhibit efficiently the Hedgehog pathway through direct antagonism of the wild-type and drug-resistant form of the Smoothened receptor. Notably, these compounds repressed the Hh-dependent growth events and the proliferation of tumor cells with aberrant activation of the Hh pathway, which plays a crucial role in development and tumorigenesis