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Palladium-Catalyzed Modular Synthesis of Thiophene-Fused Polycyclic Aromatics via Sequential C-H Activation.
Org Lett
January 2025
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. China.
A palladium-catalyzed Catellani-type [2+2+2] annulation reaction of aryl iodides, bromothiophenes, and norbornadiene, which proceeds via a tandem Heck coupling/double C-H bond activation and retro-Diels-Alder pathway to access thiophene-fused polyaromatics, is reported. The key feature of this protocol represents a NBD/NBE retaining annulation.
View Article and Find Full Text PDFPalladium-Catalyzed Tandem Reactions via Allene Intermediates for the Rapid Synthesis of a Fused Indenone-Indole Scaffold.
Org Lett
January 2025
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing 211800, China.
A palladium-catalyzed tandem reaction of 1-(2-iodophenyl)-3-arylprop-2-yn-1-ones and 1-(2-azidophenyl)propargyl ethers is developed to provide the rapid construction of a fused polycyclic indenone-indole scaffold under mild conditions. The reaction proceeds via a highly ordered process involving Sonogashira coupling, propargyl-allenyl isomerization, allene-azide cycloaddition, denitrogenation, and diradical coupling. The proposed reaction mechanism is supported by experimental and computational studies.
View Article and Find Full Text PDFPalladium-Catalyzed Tandem Reaction of β-Ketonitriles with Arylboronic Acids and Dimethyl Sulfoxide: Application to Multicomponent Synthesis of Poly-Substituted Pyridines.
J Org Chem
January 2025
State Key Laboratory of Macromolecular Drugs and Large-Scale Manufacturing, School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, P. R. China.
The Pd-catalyzed multicomponent tandem reaction of β-ketonitriles, arylboronic acids and DMSO was efficiently developed, enabling access to a variety of poly substituted pyridines. The protocol shows excellent chemoselectivity, generating nicotinonitriles or symmetrical tetrasubstituted pyridines under different conditions by tandem cyclization of enaminone intermediates with β-ketonitriles or enolates, respectively, and does not require extra ammonias. This method boasts notable advantages, such as the use of commercially available or easily prepared substrates, simple conditions, a broad substrate scope, and good functional group tolerance.
View Article and Find Full Text PDFEnantioselective Synthesis of Isoindolinone by Sequential Palladium-Catalyzed Aza-Heck/Suzuki Coupling Reaction.
Org Lett
January 2025
School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China.
We present a tandem aza-Heck/Suzuki cross-coupling reaction of -phenyl hydroxamic ethers with readily available arylboronic and alkenyl boronic acids. This protocol is enabled by a palladium catalyst paired with chiral phosphoramidite ligands, particularly under mild reaction conditions, yielding efficient and succinct synthetic routes to chiral isoindolinones with high enantioselectivity. Furthermore, this reaction exhibits excellent functional group compatibility and a rich diversity of subsequent transformations.
View Article and Find Full Text PDFPalladium-Catalyzed Tandem Cyclization of Functional Diarylalkynes and Isocyanides for the Assembly of Isochromeno[4,3-]quinolines.
J Org Chem
December 2024
Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China.
A novel strategy for the synthesis of various isochromeno[4,3-]quinolines via palladium-catalyzed tandem cyclization of functional diarylalkynes with isocyanides has been developed. This approach features excellent chemo- and regioselectivities as well as good functional group tolerance. Notably, 6-phenylimino-6-isochromeno[4,3-]quinolin-11-amines and 11-amino-6-isochromeno[4,3-]quinolin-6-ones can be selectively constructed by employing different protecting groups of functional diarylalkynes.
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