Issue 48, 2024, Issue in Progress

Phenylsulfonate as a photolabile group for intramolecular carbon–carbon cross-coupling reactions

Abstract

Efficient cyclization reactions play a pivotal role in the synthesis of extended polycyclic aromatic hydrocarbons (PAHs) and graphene nanoribbons. Although efficient reactions have been developed, a simple yet versatile method that is compatible with most functional groups is still lacking. Herein, we report the use of phenylsulfonates as a photolabile group to generate aryl radicals that undergo a radical cyclization reaction to produce triphenylene derivatives. The phenylsulfonate group proves to be a highly adaptable and robust photolabile group, and compatible with Suzuki cross-coupling conditions. Kinetic and optimization experiments have been conducted, shedding light on the potential of this reaction as a versatile tool for the synthesis of PAHs.

Graphical abstract: Phenylsulfonate as a photolabile group for intramolecular carbon–carbon cross-coupling reactions

Supplementary files

Article information

Article type
Paper
Submitted
12 Sep 2024
Accepted
31 Oct 2024
First published
05 Nov 2024
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2024,14, 35227-35231

Phenylsulfonate as a photolabile group for intramolecular carbon–carbon cross-coupling reactions

S. Plaize and J. Morin, RSC Adv., 2024, 14, 35227 DOI: 10.1039/D4RA06592A

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