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. 2024 Feb 16;89(4):2764-2770.
doi: 10.1021/acs.joc.3c02002. Epub 2024 Jan 25.

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

Carlos J Rivas  1   2 , Leandro D Mena  1   2 , María T Baumgartner  1   2 , Liliana B Jimenez  1   2
Affiliations

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

Carlos J Rivas et al. J Org Chem. .

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 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.

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