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Volume 215, 2019
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Utilising excited state organic anions for photoredox catalysis: activation of (hetero)aryl chlorides by visible light-absorbing 9-anthrolate anions

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Abstract

The tricyclic aromatic ketone 9-anthrone and its derivatives are under basic conditions in equilibrium with their corresponding anionic forms. Unlike the neutral species, the 9-anthrolate anions can be excited by blue LED light and thus, are able to initiate a photoinduced electron transfer (PET) reaction. To demonstrate the synthetic applicability of the catalytic system, various (hetero)aryl chlorides were converted in C–C and C–Het bond-forming reactions affording the corresponding arylation products in moderate to excellent yields. The reactions proceed under very mild conditions without the need for a sacrificial electron donor. Besides 9-anthrone, other closely related derivatives were synthesised and investigated concerning their ability to catalyse demanding reductive transformations. Based on spectroscopic findings and radical trapping experiments a conceivable mechanism is proposed.

Graphical abstract: Utilising excited state organic anions for photoredox catalysis: activation of (hetero)aryl chlorides by visible light-absorbing 9-anthrolate anions

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Article information


Submitted
14 Nov 2018
Accepted
05 Feb 2019
First published
05 Feb 2019

Faraday Discuss., 2019,215, 364-378
Article type
Paper

Utilising excited state organic anions for photoredox catalysis: activation of (hetero)aryl chlorides by visible light-absorbing 9-anthrolate anions

M. Schmalzbauer, I. Ghosh and B. König, Faraday Discuss., 2019, 215, 364
DOI: 10.1039/C8FD00176F

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