Issue 18, 2024

Iron-catalyzed cascade cyclization of diaryldiyn-3-ones with P(O)H compounds: a rapid method for accessing 10-phosphorylated benzo[b]fluorenones

Abstract

A new inexpensive iron-catalyzed phosphination of diaryldiyn-3-ones under mild conditions for the synthesis of 10-phosphorylated benzo[b]fluorenones is presented. The reaction is proposed to proceed via the generation of electrophilic phosphenium species (Ar2POTf) from secondary phosphine oxides in the presence of Tf2O and 2,6-lutidine, followed by cycloaddition with alkynes to form three-membered phosphirenium cation intermediates. Subsequently, a rapid intermolecular tandem cyclization occurs.

Graphical abstract: Iron-catalyzed cascade cyclization of diaryldiyn-3-ones with P(O)H compounds: a rapid method for accessing 10-phosphorylated benzo[b]fluorenones

Supplementary files

Article information

Article type
Research Article
Submitted
19 Apr 2024
Accepted
13 Jul 2024
First published
17 Jul 2024

Org. Chem. Front., 2024,11, 4997-5002

Iron-catalyzed cascade cyclization of diaryldiyn-3-ones with P(O)H compounds: a rapid method for accessing 10-phosphorylated benzo[b]fluorenones

Y. Cao, Y. Ying, J. Wu, F. Chen, G. Tang and Y. Zhao, Org. Chem. Front., 2024, 11, 4997 DOI: 10.1039/D4QO00703D

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