4.8 Article

Dehydroxylative Arylation of Alcohols via Paired Electrolysis

Journal

ORGANIC LETTERS
Volume 24, Issue 40, Pages 7476-7481

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03136

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In this study, nonactivated alcohols and arene compounds were used in an electrochemical dehydroxylative arylation reaction to construct C(sp(3))-C(sp(2)) bonds. The PIII reagent underwent single-electron anodic oxidation and cathodic reduction reactions, resulting in the generation of radical intermediates for the coupling reaction to form dehydroxylative arylated products.
Nonactivated alcohols along with arene compounds are used in electrochemical dehydroxylative arylation for constructing C(sp(3))-C(sp(2)) bonds. The PIII reagent undergoes single-electron anodic oxidation to form its radical cation, which reacts with the alcohol to produce an alkoxytriphenylphosphine radical. Through spontaneous beta-scission of the phosphoranyl radical, the C-O bond is cleaved to form an alkyl radical species, which couples with the radical anion generated by cathodic reduction of the electron-poor arene to afford the dehydroxylative arylated product.

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