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N , N -Diisopropylethylamine-Mediated Electrochemical Reduction of Azobenzenes in Dichloromethane.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2022 Nov 04; Vol. 87 (21), pp. 14536-14543. Date of Electronic Publication: 2022 Oct 21. - Publication Year :
- 2022
-
Abstract
- We report a cathodic reduction-dominated electrochemical approach for the hydrogenation of azobenzenes in dichloromethane. With cheap and readily available N , N -diisopropylethylamine as a catalytic mediator, the reaction proceeded smoothly in a simple undivided cell under constant-current electrolysis. A series of azobenzenes were successfully reduced to the corresponding hydrazobenzenes in moderate to high yields at room temperature. Preliminarily mechanistic studies indicate that solvent dichloromethane acts as a hydrogen source. The use of a common solvent as a hydrogen source, no need for stoichiometric mediators or metallic reductants, and mild conditions make this work a more straightforward and sustainable protocol for hydrogenation of azobenzenes.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 87
- Issue :
- 21
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 36269896
- Full Text :
- https://doi.org/10.1021/acs.joc.2c01949