Issue 72, 2024

A selective photoinduced radical O-alkenylation of phenols and naphthols with terminal alkynes

Abstract

The visible light-promoted O-alkenylation of phenols and naphthols with terminal alkynes is achieved using 2,4,6-tris(4-fluorophenyl)pyrylium tetrafluoroborate (T(p-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. The utility of the hydroarylated products for the synthesis of fused benzofurans via a one-pot annulation was also demonstrated. Herein, we report the first intermolecular radical hydroarylation of alkynes.

Graphical abstract: A selective photoinduced radical O-alkenylation of phenols and naphthols with terminal alkynes

Supplementary files

Article information

Article type
Communication
Submitted
31 מאי 2024
Accepted
05 אוג 2024
First published
07 אוג 2024

Chem. Commun., 2024,60, 9813-9816

A selective photoinduced radical O-alkenylation of phenols and naphthols with terminal alkynes

V. Praveen Kumar, C. S. Athira, B. Mohan, S. Priya and B. S. Sasidhar, Chem. Commun., 2024, 60, 9813 DOI: 10.1039/D4CC02555E

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