Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 28, Pages 9575-9580Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201902785
Keywords
dual catalysis; graphitic carbon nitride; heterogeneous catalysis; metallaphotoredox; photocatalysis
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Funding
- Max-Planck Society
- Liebig Fellowship of the German Chemical Industry Fund (Fonds der Chemischen Industrie, FCI)
- International Max Planck Research School on Multiscale Bio-Systems
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Cross-coupling reactions mediated by dual nickel/photocatalysis are synthetically attractive but rely mainly on expensive, non-recyclable noble-metal complexes as photocatalysts. Heterogeneous semiconductors, which are commonly used for artificial photosynthesis and wastewater treatment, are a sustainable alternative. Graphitic carbon nitrides, a class of metal-free polymers that can be easily prepared from bulk chemicals, are heterogeneous semiconductors with high potential for photocatalytic organic transformations. Here, we demonstrate that graphitic carbon nitrides in combination with nickel catalysis can induce selective C-O cross-couplings of carboxylic acids with aryl halides, yielding the respective aryl esters in excellent yield and selectivity. The heterogeneous organic photocatalyst exhibits a broad substrate scope, is able to harvest green light, and can be recycled multiple times. Insitu FTIR was used to track the reaction progress to study this transformation at different irradiation wavelengths and reaction scales.
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