The first catalytic trifluoromethoxylation of unactivated alkenes has been developed, in which Pd(CH3CN)2Cl2 was used as catalyst, AgOCF3 as trifluoromethoxide source, and Selectfluor-BF4 as oxidant. A variety of 3-OCF3 substituted piperidines were selectively obtained in good yields. Direct evidence was provided to address the facile reductive elimination of Pd(IV)-OCF3 complex to form sp(3) C-OCF3 bond.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jacs.5b10971 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Palladium-Catalyzed Intramolecular C-H Amination via Oxidative Coupling on Indole Derivatives: Access to 11-Benzo[4,5]imidazo[1,2-]indoles.
Org Lett
January 2025
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 PDFSynthesis of continuously substituted quinolines from -alkenyl aromatic isocyanides by palladium-catalyzed intramolecular imidoylative 6- cyclization.
Chem 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 PDFPalladium-Catalyzed Selective Carbonylation Reactions of -Phenylene Dihalides with Bifunctional ,-Nucleophiles.
Molecules
November 2024
Department of General and Inorganic Chemistry, University of Pécs, Ifjúság u. 6., H-7624 Pécs, Hungary.
Palladium-catalyzed carbonylation reactions of -phenylene dihalides were studied using aminoethanols as heterobifunctional ,-nucleophiles. The activity of aryl-iodide and -bromide as well as the chemoselective transformation of amine and hydroxyl functionalities were studied systematically under carbonylation conditions. Aminocarbonylation can be selectively realized under optimized conditions, enabling the formation of amide alcohols, and the challenging alkoxycarbonylation can also be proved feasible, enabling amide-ester production.
View Article and Find Full Text PDFPalladium-Catalyzed Dual C-H Arylation/Cyclization Reaction of Iodoferrocenes with -Bromobenzamides for the Construction of Arylated Isoquinolone-Fused Ferrocenes.
J Org Chem
December 2024
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen 361021, China.
We reported a palladium/norbornene-catalyzed dual intermolecular C-H arylation/intramolecular cyclization reaction of iodoferrocenes with -bromobenzamides, enabling the formation of arylated isoquinolone-fused ferrocenes in a straightforward and effective manner. This method has a broad substrate scope and good functional group compatibility, while the gram-scale reaction demonstrates the practicality of this method.
View Article and Find Full Text PDFDivergent Access to Polycyclic Fluorenofuran Systems via Palladium-Catalyzed Cascade Furan-Participated Diels-Alder Cycloaddition Reactions.
Org Lett
December 2024
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing 211800, China.
The Pd-catalyzed reaction of 1-(2-iodophenyl)-3-arylprop-2-yn-1-ones with benzene-tethered furan-ynes produces novel fused hexacyclic indenone-furan scaffolds, while the reaction with propargyl furfuryl ethers affords the pentacyclic indenone-spirodifuran system. The thiophene-containing alkynes also proceed by similar transformations. A mechanism involving the Pd-catalyzed coupling and propargylic Alder-ene reaction to generate the indenone-allene intermediate, followed by an intramolecular furan/thiophene-participated inverse electron-demand Diels-Alder reaction, is proposed.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!