Au-catalyzed chemoselective methods for synthesizing N-sulfonyl enaminones are developed. Two different isomers are obtained in a chemocontrolled manner by employing the different properties of Au(I) and Au(III) catalysts. Hydroamidation and proton-assisted carbonyl activation followed by Meyer-Schuster rearrangement are proposed as the working mechanisms for the reactions. A wide range of substrates afforded moderate to excellent yields and selectivities. These reactions represent the first examples of transition-metal-catalyzed enamine synthesis from sulfonamides and alkynes.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.7b02022 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Heterochiral Self-Discrimination Driven Dimerization of Polynuclear Gold(I)-Sulfido Complexes with Enhanced Phosphorescence.
Angew Chem Int Ed Engl
December 2024
Institute of Molecular Functional Materials, State Key Laboratory of Synthetic Chemistry, and Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, 999077, P. R. China.
Article Synopsis
- Researchers have created decanuclear chiral gold(I) sulfido clusters (S-Au and R-Au) using specialized SDP ligands.
- Mixing these chiral clusters in a 1:1 ratio yields an achiral heterodimer icosanuclear meso-cluster (meso-Au), which exhibits intense near-infrared luminescence with a peak at around 750 nm.
- The study highlights the significant increase in photoluminescence quantum yield for meso-Au (25%) compared to the chiral clusters (8%), and shows that the clustering process is influenced by solvent polarity and diphosphine ligand configuration, aiding the understanding of self-sorting in chiral assemblies.
A CD Study of a Structure-Based Selection of -Heterocyclic Bis-Carbene Gold(I) Complexes as Potential Ligands of the G-Quadruplex-Forming Human Telomeric hTel23 Sequence.
Molecules
November 2024
Department of Molecular Medicine and Medical Biotechnology, University of Napoli Federico II, Via Sergio Pansini 5, 80131 Napoli, Italy.
Herein, we report the structure-based selection via molecular docking of four -heterocyclic bis-carbene gold(I) complexes, whose potential as ligands for the hTel23 G-quadruplex structure has been investigated using circular dichroism (CD) spectroscopy, CD melting, and polyacrylamide gel electrophoresis (PAGE). The complex containing a bis(1,2,3,4,6,7,8,9-octahydro-11-11-pyridazino[1,2-a]indazol-11-yl) scaffold induces a transition from the hybrid (3 + 1) topology to a prevalent parallel G-quadruplex conformation, whereas the complex featuring a bis(2-(2-acetamidoethyl)-3-imidazo[1,5-a]pyridin-3(2)-yl) moiety disrupted the original G-quadruplex structure. These results deserve particular attention in light of the recent findings on the pathological involvements of G-quadruplexes in neurodegenerative diseases.
View Article and Find Full Text PDFUltrafast Luminescence Detection with Selective Adsorption of Carbon Disulfide in a Gold(I) Metal-Organic Framework.
Angew Chem Int Ed Engl
November 2024
Institute for Materials Research, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai, 980-8577, Japan.
Although a widely used and important industrial chemical, carbon disulfide (CS) poses a number of hazards due to its volatility and toxicity. As such, the development of multifunctional materials for the selective capture and easy recognition of CS is one of the crucial issues. Herein, we demonstrate completely selective CS adsorption among trials involving HO, alcohols, volatile organic compounds (including thiol derivatives), N, H, O, CH, CO, NO, and CO.
View Article and Find Full Text PDFGold(I) complexes of the type [AuL{κC-2-CHP(S)Ph}] [L = PTA, PPh, PPh(CH-3-SONa) and PPh(2-py)]: Synthesis, characterisation, crystal structures, and In Vitro and In Vivo anticancer properties.
Eur J Med Chem
January 2025
School of Science, STEM College, RMIT University, Melbourne, Victoria, 3001, Australia. Electronic address:
Four new mononuclear gold (I) compounds of the type [AuL{κC-2-CHP(S)Ph}] {L = PTA (1), PPh (2), PPh(CH-3-SONa) (3), and PPh(2-py) (4)} were prepared by scission of the dinuclear compound [Au{μ-2-CHP(S)Ph}] by L or via a transmetalation reaction using the organotin reagent 2-MeSnCHP(S)Ph and a suitable gold halide precursor. The cytotoxic potential of complexes 1-4 was evaluated against four human cancer cell lines of diverse cellular origin: cervical (HeLa), prostate (PC-3), non-small cell lung adenocarcinoma (A549), and fibrosarcoma (HT-1080). The in vitro cytotoxicity results showed that 1 demonstrated exceptional anticancer activity with IC values ranging from 0.
View Article and Find Full Text PDFGold(I) Complexes Based on Nonsteroidal Anti-Inflammatory Derivatives as Multi-Target Drugs against Colon Cancer.
Inorg Chem
October 2024
Departamento de Química Inorgánica, Instituto de Síntesis Química y Catálisis Homogénea-ISQCH, Universidad de Zaragoza-C.S.I.C., 50009 Zaragoza, Spain.
Targeting inflammation and the molecules involved in the inflammatory process could be an effective cancer prevention and therapy strategy. Therefore, the use of anti-inflammatory strategies, such as NSAIDs and metal-based drugs, has become a promising approach for preventing and treating cancer by targeting multiple pathways involved in tumor progression. The present work describes new phosphane gold(I) complexes derived from nonsteroidal anti-inflammatory drugs as multitarget drugs against colon cancer.
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!