4.6 Article

Deoxygenative coupling of alcohols with aromatic nitriles enabled by direct visible light excitation

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ORGANIC & BIOMOLECULAR CHEMISTRY
卷 21, 期 47, 页码 9316-9320

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d3ob01676e

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A general and practical protocol for visible-light-driven deoxygenative coupling of alcohols with aromatic nitriles in the absence of external photocatalysts is presented. The platform utilizes a hydroxyl activation strategy with carbon disulfide and accommodates a broad scope of alcohols and aryl nitriles, delivering various alkyl-substituted arenes. Mechanism studies reveal that a single electron transfer event between a photoexcited aryl nitrile and a xanthate anion is crucial for the transformation.
A general and practical protocol is presented for visible-light-driven deoxygenative coupling of alcohols with aromatic nitriles in the absence of external photocatalysts. Utilizing a hydroxyl activation strategy with carbon disulfide, this C(sp3)-C(sp2) constructing platform accommodates a broad scope of alcohols and aryl nitriles to deliver various alkyl-substituted arenes. Mechanism studies show that a single electron transfer event between a photoexcited aryl nitrile and a xanthate anion is key to the transformation. A general and practical protocol is presented for visible-light-driven deoxygenative coupling of alcohols with aromatic nitriles in the absence of external photocatalysts.

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