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

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 SRN1 mechanism. We present herein a new perspective, suggesting that a single-electron-transfer aromatic nu...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-02, Vol.89 (4), p.2764-2770
Main Authors: Rivas, Carlos J., Mena, Leandro D., Baumgartner, María T., Jimenez, Liliana B.
Format: Article
Language:English
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Summary: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 SRN1 mechanism. We present herein a new perspective, suggesting that a single-electron-transfer aromatic nucleophilic substitution (SeT-SNAr) 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 O-arylated PBIs.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02002