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Direct Transformation of Esters into Heterocyclic Fluorophores.

Angewandte Chemie (International ed. in English) (2017-12-19)
Christian Fischer, Christof Sparr
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
9-(2,6-Dimethylphenyl)-1-methoxy-10-phenylacridinium bromide, 95%
Sigma-Aldrich
7-(Dimethylamino)-1-methoxy-9-(naphthalen-1-yl)-10-phenylacridinium bromide, 95%
Sigma-Aldrich
3,6-Bis(dimethylamino)-9-mesityl-10-methylacridinium bromide, ≥95%
Sigma-Aldrich
6-(Dimethylamino)-9-(2,6-dimethylphenyl)-1-methoxy-10-phenylacridinium bromide, ≥95%