Katritzky salts have emerged as effective alkyl radical sources upon metal- or photocatalysis. These are typically prepared from the corresponding triarylpyrylium ions, in turn an important class of photocatalysts for small molecules synthesis and photopolymerization. Here, a flow method for the rapid synthesis of both pyrylium and Katrizky salts in a telescoped fashion is reported. Moreover, several pyrylium salts were tested in the photoinduced RAFT polymerization of vinyl ethers under flow and batch conditions.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8041383 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.1c00178 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Towards Designer Photocatalysts: Structure-Property Relationships in 2,6-Diaryl-pyryliums.
Chemistry
November 2024
Department of Chemistry, University of Wisconsin-Platteville, 1 University Plaza, Platteville, WI 53818, USA.
Fully organic photocatalyst systems are highly attractive, not merely because they are transition-metal free, but more importantly due to their unique and often potent reactivity. A detailed understanding of the various redox states, both ground and excited state, and specifically what structural parameters control them is therefore crucial for harnessing the full potential of these systems in organic synthesis. However, unlike their organometallic counterparts, detailed structure-property relationships for organic photocatalysts are largely absent from the literature.
View Article and Find Full Text PDFSynthesis, Optical Spectroscopy, and Laser and Biomedical Imaging Application Potential of 2,4,6-Triphenylpyrylium Tetrachloroferrate and Its Derivatives.
J Phys Chem B
October 2024
Department of Pharmacology and Cancer Biology, Duke University, Durham, North Carolina 27705, United States.
Synthesis, optical spectroscopic properties, two-photon (TP) absorption-induced fluorescence, and laser and bioimaging application potentials of 2,4,6-triphenylpyrylium tetrachloroferrate (),4-(4-methoxyphenyl)-2,6-diphenylpyrylium tetrachloroferrate (), 2,6-bis(4-methoxyphenyl)-4-phenylpyrylium tetrachloroferrate (), and 2,4,6-tris(4-methoxyphenyl)pyrylium tetrachloroferrate () are presented. The synthesis involves the conversion of pyrylium tosylates to pyrylium chlorides, followed by transformation into - on heating to reflux with FeCl in acetonitrile. They are characterized using H and C NMR spectra in CDOD, and FTIR and Raman spectroscopic techniques.
View Article and Find Full Text PDFA selective photoinduced radical -alkenylation of phenols and naphthols with terminal alkynes.
Chem Commun (Camb)
September 2024
Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Thiruvananthapuram 695019, Kerala, India.
The visible light-promoted -alkenylation of phenols and naphthols with terminal alkynes is achieved using 2,4,6-tris(4-fluorophenyl)pyrylium tetrafluoroborate (T(-F)PPT) as a photocatalyst at room temperature without the need of any external ligand or additive. Apart from its excellent functional group tolerance, the protocol described herein represents an appealing alternative strategy to classical transition-metal catalysed hydroarylation reactions. Mechanistic investigations revealed that the reaction involves a radical pathway.
View Article and Find Full Text PDFNovel convenient 2-step synthesis of pyrido[1,2-]indoles from pyrylium salts and -bromoanilines.
Org Biomol Chem
August 2024
A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Leninsky Prospect 29, Moscow, 119991, Russia.
A novel convenient 2-step synthesis of substituted pyrido[1,2-]indoles is developed starting from easily available pyrylium tetrafluoroborates and -bromoanilines. A conversion of the pyrylium tetrafluoroborates to pyridinium ones followed by their palladium catalyzed intramolecular cyclization allows the formation of 24 examples of N-fused heterocycles. A one-pot two-stage cyclization procedure was developed.
View Article and Find Full Text PDFMechanochemical synthesis of aromatic ketones: pyrylium tetrafluoroborate mediated deaminative arylation of amides.
Chem Sci
June 2024
Department of Chemistry, Faculty of Natural Sciences, Matej Bel University Tajovského 40 97401 Banska Bystrica Slovakia
A new method has been introduced that is able to tackle the complexities of N-C(O) activation in amide moieties through utilization of pyrylium tetrafluoroborate in a mechanochemical setting, where amide bonds undergo activation and subsequent conversion to biaryl ketones. Due to the employment of a mechanochemical setting, the reaction conforms to green chemistry principles, offering an environmentally friendly approach to traditional amide derivatization techniques that rely on transition metals to achieve further functionalization.
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!