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 may. 2024
Accepted
05 ago. 2024
First published
07 ago. 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements