Herein, we report sodium iodide (NaI)-catalyzed decarboxylative C-H alkylation of azauracils with -hydroxyphthalimide (NHPI) esters facilitated by visible light activation of catalytic electron donor-acceptor (EDA) complexes. Control experiments and density functional theory calculations suggest that the decarboxylative coupling reaction proceeds via a transiently assembled EDA complex between the NHPI ester and NaI in ,-dimethylacetamide solvent. This synthetic method efficiently applies to primary, secondary, and tertiary NHPI esters under mild, photocatalyst-free, and redox-neutral conditions, achieving high yields of the desired alkylated azauracils.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.4c02177 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Mechanisms and Origins of Regioselectivity in Rare-Earth-Catalyzed C-H Functionalization of Anisoles and Thioanisoles.
Inorg Chem
March 2025
Institutes of Physical Science and Information Technology, Anhui University, Hefei 230601, China.
The direct catalytic C-H functionalization of aromatic compounds such as anisoles and thioanisoles is of great interest and significance. However, achieving precise regioselectivity remains a major challenge. In this study, we conducted comprehensive density functional theory calculations to explore the mechanisms of rare-earth-catalyzed regioselective C-H alkylation, borylation, and silylation of anisole and thioanisole.
View Article and Find Full Text PDFVisible-Light-Induced Divergent C-H Esterification/Alkylation of Quinoxalin-2(1)-ones with Aldehydes under Mild Conditions.
Org Lett
March 2025
College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Zhejiang Key Laboratory of Organosilicon Material Technology, Hangzhou Normal University, Hangzhou 311121, China.
Herein, we introduce an efficient and straightforward strategy for the selective C-H esterification and alkylation of quinoxalin-2(1)-ones with aldehydes. A key feature of our study is the ability to perform both C-H esterification and alkylation using different types of aldehydes. The reaction system is highly compatible with a range of quinoxalin-2(1)-ones and aldehydes, yielding C3-esterified and C3-alkylated products in moderate-to-good yields.
View Article and Find Full Text PDFAn archetype of hydrogen bonding observed in cationic dimers of carboxy-functionalized ionic liquids by means of NMR solid state spectroscopy - reminiscent of salt bridges, peptides and DNA.
Phys Chem Chem Phys
March 2025
Universität Rostock, Institut für Chemie, Abteilung für Physikalische Chemie, Dr-Lorenz-Weg 2, Rostock 18059, Germany.
Ion pair formation is a fundamental concept in chemistry. The association between ions of opposite charge is widely used in synthesis and catalysis. In contrast, there is little evidence for the formation of cationic or anionic dimers in solution.
View Article and Find Full Text PDFStructural and dielectric properties of electrospun P(VDF-TrFE) and P3HT filled with copper oxide nanofillers.
Sci Rep
March 2025
ESCs Research Lab, Physics Department, Faculty of Science, Mansoura University, Mansoura, Egypt.
Nanofibers based on polyvinylidene fluoride-trifluoroethylene/poly(3-hexylthiophene) (P(VDF-TrFE)/P3HT) containing copper oxide nanoparticles (CuO NPs) were fabricated using the electrospinning technique. Scanning electron microscope (SEM) images revealed smooth, bead-free solid nanofibers of 34-100 nm diameters. X-ray diffraction (XRD) analysis shows the ferroelectric β phase of P(VDF-TrFE) with a wide diffraction pattern.
View Article and Find Full Text PDFPalladium-Catalyzed meta-C-H Alkoxylation and Amidation via the Polarity Reversal of Nucleophilic Reagents.
Angew Chem Int Ed Engl
March 2025
Lanzhou University, Chemistry and Chemical Engineering, Lanzhou University, Tianshui Road, Lanzhou, China, 730000, Lanzhou, CHINA.
Norbornene-mediated remote meta-selective C-H functionalizations of arenes have been limited to relatively weakly electronegative and "soft" species, such as aryl, alkyl, and alkylamino moieties. Herein, we describe the first example of the use of a nucleophilic reagent, such as an alcohol or amide, to replace the electrophilic reagent during the palladium-catalyzed meta-C-H alkoxylation or amidation reaction of an arene. The reaction conditions are mild and highly site-selective, thereby facilitating the direct introduction of natural products or drug molecules containing hydroxyl or amido groups at the meta-positions of arenes.
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!