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-Substitution of Perylene Bisimides with Bidentate Nucleophiles: The Case of Aryloxide Anions. | LitMetric

-Substitution of Perylene Bisimides with Bidentate Nucleophiles: The Case of Aryloxide Anions.

J Org Chem

Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Haya de la Torre y Medina Allende, Ciudad Universitaria. Córdoba, X5000HUA, Argentina.

Published: February 2024

AI Article Synopsis

Article Abstract

In this study, we delve into the regioselectivity of nucleophilic reactions involving brominated perylene bisimides (PBIs) and various bidentate aryloxide anions, previously associated with an S1 mechanism. We present herein a new perspective, suggesting that a single-electron-transfer aromatic nucleophilic substitution (SeT-SAr) mechanism is a more plausible scenario. Our study reveals the favorable impact of photostimulation on reaction yields, making our method a convenient approach for accessing arylated PBIs.

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Source
http://dx.doi.org/10.1021/acs.joc.3c02002DOI Listing

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