Reductive Electrophotocatalysis: Merging Electricity and Light To Achieve Extreme Reduction Potentials

We describe a new electrophotocatalytic strategy that harnesses the power of light and electricity to generate an excited radical anion with a reducing potential of −3.2 V vs SCE, which can be used to activate substrates with very high reduction potentials (E red ≈ −1.9 to −2.9 V). The resultant ary...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 142; no. 5; pp. 2087 - 2092
Main Authors Kim, Hyunwoo, Kim, Hyungjun, Lambert, Tristan H, Lin, Song
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.02.2020
Amer Chemical Soc
Subjects
aromatic compounds
Chemistry
Chemistry, Multidisciplinary
electricity
free radicals
photocatalysis
Physical Sciences
Science & Technology
FUNCTIONALIZATION
UNACTIVATED ALKYL
CATALYSIS
ACTIVATION
HALOARENES
PHOTOCHEMISTRY
ARYL IODIDES
SINGLE-ELECTRON TRANSFER
METAL-FREE
BORYLATION
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Summary:We describe a new electrophotocatalytic strategy that harnesses the power of light and electricity to generate an excited radical anion with a reducing potential of −3.2 V vs SCE, which can be used to activate substrates with very high reduction potentials (E red ≈ −1.9 to −2.9 V). The resultant aryl radicals can be engaged in various synthetically useful transformations to furnish arylboronate, arylstannane, and biaryl products.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.9b10678