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Herein, we developed a novel radical cascade phosphorylation/cyclization strategy to access phosphorus-containing diazocine-fused carbazoles in moderate to good yields, offering expanded opportunities for the exploration of biologically active molecules. This method features metal-free photochemical tandem, mild conditions, broad substrate scopes, and scale-up ability. Mechanistic experiments implied that this photocatalyzed phosphorylation/cyclization reaction was realized by a sequence of EnT/SET/SET/radical addition/cyclization/SET/deprotonation processes.
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http://dx.doi.org/10.1021/acs.joc.5c00713 | DOI Listing |
J Org Chem
May 2025
School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, PR China.
Herein, we developed a novel radical cascade phosphorylation/cyclization strategy to access phosphorus-containing diazocine-fused carbazoles in moderate to good yields, offering expanded opportunities for the exploration of biologically active molecules. This method features metal-free photochemical tandem, mild conditions, broad substrate scopes, and scale-up ability. Mechanistic experiments implied that this photocatalyzed phosphorylation/cyclization reaction was realized by a sequence of EnT/SET/SET/radical addition/cyclization/SET/deprotonation processes.
View Article and Find Full Text PDFChem Commun (Camb)
March 2025
Key Laboratory of Functional Molecular Solids, Ministry of Education, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China.
A novel strategy of cascade phosphorylation cyclization of 2-isocyanobenzonitrile with phosphine oxide a DBU-promoted process has been developed. A series of phosphorylated 3-aminoindoles were constructed by forming C-C, C-P and N-P bonds and an amino group in one pot. A plausible reaction mechanism has been proposed based on step-by-step control experiments and P NMR analysis.
View Article and Find Full Text PDFJ Org Chem
January 2025
School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China.
A novel regioselective manganese(III)-mediated radical cascade cyclization of N-propargyl enamides with various H-phosphine oxides, H-phosphinates and H-phosphonates was developed. Mechanistic studies show that the reaction is mainly composed of the selective addition of phosphonyl radical to C≡C bond and the intramolecular 6--trig cyclization of vinyl radical. Utilizing this protocol, we successfully synthesized a diverse range of 3-phosphorylpyridines in high efficiency with good functional group compatibility and simple operation.
View Article and Find Full Text PDFOrg Lett
November 2022
Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, China.
3-(2-(Ethynyl)phenyl)quinazolinones were designed and synthesized as a class of novel and efficient skeletons for phosphorylation/cyclization reactions. Under visible light irradiation, a series of phosphorylated quinolino[2,1-]quinazolinones (35 examples, up to 87% yield) were first synthesized from 3-(2-(ethynyl)phenyl)quinazolinones and diarylphosphine oxides by using 4CzIPN as a photocatalyst under mild conditions. This reaction was also applicable under sunlight irradiation.
View Article and Find Full Text PDFJ Org Chem
November 2022
Green Catalysis Center, College of Chemistry, Zhengzhou University, Kexue Road No. 100, Zhengzhou 450001, China.
A visible-light-induced persulfate-promoted cascade phosphorylation/cyclization reaction to access various phosphorylated pyrrolo[1,2-]indolediones under mild conditions was developed. Notably, the transformation was carried out with diethyl carbonate/HO as a green medium at room temperature. More impressively, traditional metal catalysts and photocatalysts could be effectively avoided.
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