Electrochemical Dimerization of <i>o</i>-Aminophenols and Hydrogen Borrowing-like Cascade to Synthesize N-Monoalkylated Aminophenoxazinones via Paired Electrolysis

A novel electrocatalytic dimerization of <i>o</i>-aminphenols and a hydrogen borrowing-like cascade for synthesizing N-monoalkylated aminophenoxazinones have been developed. This electrocatalytic reaction uses a constant current mode in an undivided cell and is free of metal catalysis, open to the air, and eco-friendly. In particular, this protocol exhibits a wide substrate range and provides versatile N-monoalkylated aminophenoxazinones in medium to good yields. The results of our mechanistic research reveal that this protocol involves a cascade of electrochemical cyclocondensation of <i>o</i>-aminphenols and the hydrogen transfer process via paired electrolysis.

Authors

Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-09-10
DOI
https://doi.org/10.1021/acs.joc.4c01130
Citations
1
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
0.16
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article

Electrochemical Dimerization of o-Aminophenols and Hydrogen Borrowing-like Cascade to Synthesize N-Monoalkylated Aminophenoxazinones via Paired Electrolysis

Ganpeng Li, Ye Zhou, Yonghui He, Jiahui Fan et al.
1 citations
The Journal of Organic Chemistry
Asymmetric Hydrogenation and Catalysis
0.16
article

Electrochemical Dimerization of o-Aminophenols and Hydrogen Borrowing-like Cascade to Synthesize N-Monoalkylated Aminophenoxazinones via Paired Electrolysis

Ganpeng Li, Ye Zhou, Yonghui He, Jiahui Fan, Jun Gao, Xiaojing Zhao
article en
1 citations

Abstract

A novel electrocatalytic dimerization of <i>o</i>-aminphenols and a hydrogen borrowing-like cascade for synthesizing N-monoalkylated aminophenoxazinones have been developed. This electrocatalytic reaction uses a constant current mode in an undivided cell and is free of metal catalysis, open to the air, and eco-friendly. In particular, this protocol exhibits a wide substrate range and provides versatile N-monoalkylated aminophenoxazinones in medium to good yields. The results of our mechanistic research reveal that this protocol involves a cascade of electrochemical cyclocondensation of <i>o</i>-aminphenols and the hydrogen transfer process via paired electrolysis.

The Journal of Organic ChemistryVol. 89(18)
Openalex Percentile: Top 58%
Asymmetric Hydrogenation and Catalysis
0.16
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