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Direct Transformation of Esters into Heterocyclic Fluorophores
Author(s) -
Fischer Christian,
Sparr Christof
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201711296
Subject(s) - chemistry , bifunctional , combinatorial chemistry , reagent , catalysis , fluorescence , heteroatom , organic chemistry , ring (chemistry) , physics , quantum mechanics
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.