A facile electrosynthesis of N-acyl benzotriazoles from aldehydes and benzotriazole. (6th July 2022)

• Record Type: Journal Article
• Authors: Feng, Jianling; Wang, Qiang; Duan, Ruomeng; Li, Huadeng; Zheng, Ke; Wang, Xiaoxia; Xie, Guanqun
• Is Part Of: Tetrahedron letters. Volume 101(2022)
• Publication Date: 2022-07-06
• Subjects: N-acyl benzotriazoles -- Electrosynthesis -- Aldehyde -- One-pot -- Esterification; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.153904
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A mild electrosynthesis of N -acylbenzotriazoles has been developed using aromatic aldehydes and benzotriazole as starting materials. The electrochemical oxidation provided environmental friendly syntheses in that the use of superstoichiometric chemical oxidants or corrosive/toxic reagents were avoided and waste production could be significantly reduced. One-pot synthesis of phenolic esters from an aldehyde, benzotriazole and phenol has been achieved under the electricity-on and -off combination conditions. Abstract: An electrochemical synthesis of N -acylbenzotriazoles has been developed under mild conditions with good to excellent yields using aldehydes and benzotriazole as starting materials. In addition, a one-pot reaction of aldehyde, benzotriazole and phenol has been achieved affording phenolic esters in moderate yields under the combination of electricity-on/off conditions, where N -acyl benzotriazole acted as the benign acylating reagent. It is noteworthy the research provided environmental friendly syntheses in that no superstoichiometric hazardous chemical oxidants were required, corrosive/toxic reagents have been avoided and waste production has significantly been reduced. The key of the electrochemical synthesis involves the oxidation of benzotriazole-aldehyde adduct by phthalimido- N -oxy (PINO), which was generated by N -hydroxyphthalimide (NHPI) as a redox mediator.