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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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Publication details

The article was received on 14 Nov 2018, accepted on 05 Feb 2019 and first published on 05 Feb 2019


Article type: Paper
DOI: 10.1039/C8FD00176F
Citation: Faraday Discuss., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C8FD00176F

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