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Article Abstract

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.5c00713DOI Listing

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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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DBU-promoted cascade phosphorylation/cyclization for the synthesis of phosphorylated 3-aminoindoles.

Chem 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.

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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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