A new, visible light-catalyzed, one-pot and one-step reaction is successfully employed to design well-controlled side-chain functionalized polymers, by the combination of ambient temperature revisible addtion-fragmentation chain transfer (RAFT) polymerization and click chemistry. Polymerizations are well controlled in a living way under the irradiation of visible light-emitting diode (LED) light without photocatalyst and initiator, using the trithiocarbonate agent as iniferter (initiator-transfer agent-terminator) agent at ambient temperature. Fourier transfer infrared spectroscopy (FT-IR), NMR, and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) data confirm the successful one-pot reaction. Compared to the reported zero-valent metal-catalyzed one-pot reaction, the polymerization rate is much faster than that of the click reaction, and the visible light-catalyzed one-pot reaction can be freely and easily regulated by turning on and off the light.
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http://dx.doi.org/10.1002/marc.201600004 | DOI Listing |
Sci Rep
January 2025
Department of Chemistry, Yazd University, Yazd, Iran.
A new humic acid-based nanomagnetic copper(II) composite was prepared and used as an eco-friendly recoverable catalyst for synthesizing 1,4-disubstituted 1,2,3-triazoles. The synthesis was done via the three-component click reaction of alkyl halide, sodium azide, and terminal alkyne with good to excellent yield. A simple magnetic copper acetate composite, FeO@HA-Cu(OAc), was prepared using humic acid and characterized by SEM, TEM, XRD, EDX, EDS-mapping, VSM, TGA, AAS, and FT-IR.
View Article and Find Full Text PDFChem Asian J
January 2025
Chiang Mai University, Chemistry, 239 Huay Kaew Road, Muang District, 50200, Chiang Mai, THAILAND.
The Ph3P-I2-mediated reactions between isatins and amines were extensively investigated leading to the discovery of highly selective and divergent routes toward the synthesis of two distinct classes of indole-based frameworks. Through a strategic design of the reaction paths, we overcome potential side reactions to achieve convenient and straightforward one-pot methods to access either indoloquinazolines with C-12 carboxamide or 2-aminosubstituted indol-3-ones using the same reagent system. Mechanistic studies reveal the role of Ph3P-I2 in governing product selectivity, providing an efficient route to novel fused-indolone derivatives with promising applications in drug discovery and medicinal chemistry.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Molecular Synthesis Center, Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China.
2-Deoxy-β-glycosides are essential components of natural products and pharmaceuticals; however, the corresponding 2-deoxy-β-glycosidic bonds are challenging to chemically construct. Herein, we describe an efficient catalytic protocol for synthesizing 2-deoxy-β-glycosides via either IPrAuNTf-catalyzed activation of a unique 1,2--positioned C2--propargyl xanthate (OSPX) leaving group or (PhO)PAuNTf-catalyzed activation of a 1,2--C2--alkynylbenzoate (OABz) substituent of the corresponding thioglycosides. These activation processes trigger 1,2-alkyl/arylthio-migration glycosylation, enabling the synthesis of structurally diverse 2-deoxy-β-glycosides under mild reaction conditions.
View Article and Find Full Text PDFOrg Lett
January 2025
Max-Planck-Institute for Chemical Energy Conversion, Stiftstraße 34-36, 45470 Mülheim an der Ruhr, Germany.
An electrochemical one-pot synthesis of enaminyl sulfonate esters was established, featuring a quasidivided cell under constant current conditions. The multicomponent reaction utilizes simple and readily available alkylamines and an easy-to-use stock solution of SO and alcohols. Omission of additional supporting electrolyte through in-situ-generated monoalkylsulfite facilitates the downstream processing.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
School of Chemistry and Chemical Engineering, Yangzhou University, Siwangting Road 180, 225002, Yangzhou, China.
As fundamental structural scaffolds in numerous natural products and pharmaceutical molecules, the construction of cyclohexenone architectures has remained a pivotal focus in organic chemistry. However, established strategies to synthesize cyclohexenone derivatives Dowd-Beckwith ring-expansion reaction invariably involve the use of transition metals and photoirradiation. Herein, we present a novel transition-metal- and photoirradiation-free pathway to access such structures from α-iodomethyl β-keto esters with electron-rich arenediazonium salts as inexpensive radical initiators and oxidants under mild reaction conditions.
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