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Palladium catalyzed stereoselective intramolecular [3 + 2] cycloaddition reactions of () & ()-ene-vinylidenecyclopropanes.
Org Biomol Chem
June 2024
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
Article Synopsis
- - A new reaction method using palladium that opens and closes rings has been developed for specific types of compounds, known as vinylidenecyclopropanes, to create complex bicyclic structures.
- - The process involves an intramolecular cycloaddition that relies on a bulky biaryl phosphine ligand, leading to the formation of fused bicyclic products with strong control over the stereochemistry.
- - The study suggests a reasonable mechanism for this reaction, supported by earlier research and advanced computational methods, indicating a wider applicability and tolerance for various functional groups in the substrate.
Palladium-catalyzed denitrogenation/vinylation of benzotriazinones with vinylene carbonate.
Chem Commun (Camb)
March 2024
Key Laboratory of Chemical Additives for China National Light Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China.
Herein, a novel Pd-catalyzed denitrogenation/vinylation of benzotriazinones using vinylene carbonate as the vinylation reagent is reported. This transformation demonstrates an unprecedented skeletal editing approach, effectively converting NN to CC fragments and synthesizing a collection of isoquinolinones with broad-spectrum functional group tolerance. Moreover, the quite concise reaction system and late-stage modification of bioactive molecules comprehensively underscore the practical potential of this protocol.
View Article and Find Full Text PDFPalladium-Catalyzed Skeletal Rearrangement of Substituted 2-Silylaryl Triflates via 1,5-C-Pd/C-Si Bond Exchange.
Angew Chem Int Ed Engl
December 2023
Division of Chemistry, Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan.
A palladium-catalyzed skeletal rearrangement of 2-(2-allylarylsilyl)aryl triflates has been developed to give highly fused tetrahydrophenanthrosilole derivatives via unprecedented 1,5-C-Pd/C-Si bond exchange. The reaction pathways can be switched toward 4-membered ring-forming C(sp )-H alkylation by tuning the reaction conditions to give completely different products, fused dihydrodibenzosilepin derivatives, from the same starting materials. The inspection of the reaction conditions revealed the importance of carboxylates in promoting the C-Pd/C-Si bond exchange.
View Article and Find Full Text PDFTotal Synthesis of Metaphanine and Oxoepistephamiersine.
Angew Chem Int Ed Engl
October 2023
Key Laboratory of Applied Surface and Colloid Chemistry & School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 West Chang'an Ave, Xi'an, 710119, China.
Herein, we report a concise and divergent synthesis of the complex hasubanan alkaloids metaphanine and oxoepistephamiersine from commercially available and inexpensive cyclohexanedione monoethylene acetal. Our synthesis features a palladium-catalyzed cascade cyclization reaction to set the tricyclic carbon framework of the desired molecules, a regioselective Baeyer-Villiger oxidation followed by a MeNH triggered skeletal reorganization cascade to construct the benzannulated aza[4.4.
View Article and Find Full Text PDFThe cyclopenta[ b]indole moiety represents a key skeletal unit in several natural and synthetic compounds that exhibit diverse biological properties. We described herein a two-step sequence for synthesizing cyclopenta[ b]indoles with great structural diversity in overall yields up to 37%. The key step was a palladium-catalyzed oxidative annulation of 3-alkylindoles (Fujiwara-Moritani reaction).
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