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

RIVAS, CARLOS JAVIER; MENA, LEANDRO; BAUMGARTNER, MARÍA TERESA; JIMENEZ, LILIANA BEATRIZ

Journal of Organic Chemistry

American Chemical Society

Lugar: Washington; Año: 2024 vol. 89 p. 2764 - 2770

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.