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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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 142; no. 5; pp. 2093 - 2099
Main Authors Cowper, Nicholas G. W, Chernowsky, Colleen P, Williams, Oliver P, Wickens, Zachary K
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.02.2020
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Multidisciplinary
Chlorides - chemistry
Electrons
Oxidation-Reduction
Photochemical Processes
Physical Sciences
Science & Technology
HALIDES
FUNCTIONALIZATION
ACTIVATION
DIRECT ARYLATION
REDUCTION
VISIBLE-LIGHT PHOTOREDOX
ANION-RADICALS
DRIVEN
BOND
METAL-COMPLEXES
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Summary: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.
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N.G.W.C. and C.P.C. contributed equally.
Author Contributions
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.9b12328