Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 34, Pages 14275-14280Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202005724
Keywords
C-H functionalization; electrochemistry; heterocycles; photoelectrochemistry; radical reactions
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Funding
- MOST [2016YFA0204100]
- NSFC [21672178, 21971213]
- Fundamental Research Funds for the Central Universities
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Heteroarenes are structural motifs found in many bioactive compounds and functional materials. Dehydrogenative cross-coupling of heteroarenes with aliphatic C-H bonds provides straightforward access to functionalized heteroarenes from readily available materials. Established methods employ stoichiometric chemical oxidants under conditions of heating or light irradiation. By merging electrochemistry and photochemistry, we have achieved efficient photoelectrochemical dehydrogenative cross-coupling of heteroarenes and C(sp(3))-H donors through H(2)evolution, without the addition of metal catalysts or chemical oxidants. Mechanistically, the C(sp(3))-H donor is converted to a nucleophilic carbon radical through H-atom transfer with chlorine atom, which is produced by light irradiation of anodically generated Cl(2)from Cl-. The carbon radical then undergoes radical substitution to the heteroarene to afford alkylated heteroarene products.
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