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Electrochemical synthesis of 2-alkyl-4-phenylalkan-2-ols via cathodic reductive coupling of alkynes with unactivated aliphatic ketones.

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Herein, we present an efficient electrochemical method for synthesizing 2-alkyl-4-phenylalkan-2-ols through an electrochemically driven cathodic reductive coupling of the terminal and internal acetylenes with unactivated aliphatic ketones under mild conditions.… Click to show full abstract

Herein, we present an efficient electrochemical method for synthesizing 2-alkyl-4-phenylalkan-2-ols through an electrochemically driven cathodic reductive coupling of the terminal and internal acetylenes with unactivated aliphatic ketones under mild conditions. The process proceeds through a ketyl radical, which then activates the aryl acetylene and causes complete reduction of the triple bond of the acetylene moiety. This strategy is environmentally benign and exhibits a broad substrate scope with ubiquitously available starting materials.

Keywords: aliphatic ketones; reductive coupling; cathodic reductive; unactivated aliphatic; alkyl phenylalkan; phenylalkan ols

Journal Title: Chemical communications
Year Published: 2023

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