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Synthesis 2023; 55(18): 2969-2978
DOI: 10.1055/a-1992-7066
DOI: 10.1055/a-1992-7066
paper
Special Issue Electrochemical Organic Synthesis
Electrochemical Benzylic C(sp3)–H Amidation via Ritter-Type Reaction in the Absence of External Mediator and Oxidant
This work was supported by the National Natural Science Foundation of China (Project 21672104, 21502097) and the Priority Academic Program Development of Jiangsu Higher Education Institutions.
This work is dedicated to Professor Guo-Qiang Lin on his 80th birthday.
Abstract
A straightforward method involving electrochemical Ritter-type amidation of alkylarenes in the absence of external mediator and oxidant is described. This direct benzylic C(sp3)–H amidation utilizes cheap CH3CN or other nitriles as the nitrogen source and trace amount of H2O in the solvent as the oxygen and hydrogen source. A wide range of alkylarenes were found to be compatible, providing a variety of N-benzyl-substituted amides in moderate to good yields.
Key words
electrochemical oxidation - benzylic C(sp3)–H amidation - Ritter-type reaction - external mediator free - oxidant free - N-benzylamidesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1992-7066.
- Supporting Information
Publication History
Received: 16 November 2022
Accepted after revision: 05 December 2022
Accepted Manuscript online:
05 December 2022
Article published online:
03 January 2023
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For selected examples, see:
For partial examples and reviews on electrochemical C(sp3)–H functionalization, see: