The visible-light-promoted deoxygenative radical heteroarylation of alcohols was achieved in the absence of any external photosensitizers. The processes occur through the generation of xanthate salts from alcohols, followed by SET and fragmentation, delivering alkyl radicals to react with heteroaryl sulfones. This method is amenable for a wide range of alcohols with good functional group tolerance, providing a practical strategy for the alkylation of benzo-heteroaromatics.
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December 2023
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(sp)-C(sp) 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.
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