Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 9, Pages 2436-2440Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201711296
Keywords
carboxylic acid esters; fluorophores; Grignard reaction; organomagnesium reagents; photoredox catalysis
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Funding
- Swiss National Science Foundation [BSSGI0-155902/1]
- University of Basel
- NCCR Molecular Systems Engineering
- Swiss National Science Foundation (SNF) [BSSGI0_155902] Funding Source: Swiss National Science Foundation (SNF)
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Despite the manifold use of heterocyclic fluorophores, only a fraction of the desired dye diversity can be accessed by contemporary synthetic approaches. Herein, we describe a modular method that converts various carboxylic acid esters directly into a broad spectrum of heteroanthrylium fluorophores. The double addition of heteroatom-bridged 1,5-bifunctional organomagnesium reagents to esters leads to the formation of acridinium, xanthylium, and SiR fluorophores after dehydrative acidic work-up. This one-step synthetic method provides access to organophotoredox catalysts for dual catalysis with nickel and dyes amenable to fluorescence enhancement.
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