Issue 20, 2023

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
14 Dec 2022
Accepted
09 Feb 2023
First published
17 Feb 2023

Chem. Commun., 2023,59, 2915-2918

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

A. B. Dapkekar and G. Satyanarayana, Chem. Commun., 2023, 59, 2915 DOI: 10.1039/D2CC06819B

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