Potent Reductants via Electron-Primed Photoredox Catalysis: Unlocking Aryl Chlorides for Radical Coupling

We describe a new catalytic strategy to transcend the energetic limitations of visible light by electrochemically priming a photocatalyst prior to excitation. This new catalytic system is able to productively engage aryl chlorides with reduction potentials hundreds of millivolts beyond the potential...

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Veröffentlicht in:	Journal of the American Chemical Society 2020-02, Vol.142 (5), p.2093-2099
Hauptverfasser:	Cowper, Nicholas G. W, Chernowsky, Colleen P, Williams, Oliver P, Wickens, Zachary K
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Chlorides - chemistry Electrons Oxidation-Reduction Photochemical Processes
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container_end_page	2099
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container_title	Journal of the American Chemical Society
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creator	Cowper, Nicholas G. W Chernowsky, Colleen P Williams, Oliver P Wickens, Zachary K
description	We describe a new catalytic strategy to transcend the energetic limitations of visible light by electrochemically priming a photocatalyst prior to excitation. This new catalytic system is able to productively engage aryl chlorides with reduction potentials hundreds of millivolts beyond the potential of Na0 in productive radical coupling reactions. The aryl radicals produced via this strategy can be leveraged for both carbon–carbon and carbon–heteroatom bond-forming reactions. Through direct comparison, we illustrate the reactivity and selectivity advantages of this approach relative to electrolysis and photoredox catalysis.
doi_str_mv	10.1021/jacs.9b12328
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subjects	Catalysis Chlorides - chemistry Electrons Oxidation-Reduction Photochemical Processes
title	Potent Reductants via Electron-Primed Photoredox Catalysis: Unlocking Aryl Chlorides for Radical Coupling
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