Current Organic Synthesis

L.-N. He
Nankai University
P.R. China


Electrochemical Synthesis of Polyfunctionalized Indoles in Aqueous Medium from Catechols and Ketene N,S-acetals

Author(s): Xiao-Guang Gao, Ni-Tao Zhanga, Cheng-Chu Zeng, Yong-Dong Liu, Li-Ming Hu and Hong-Yu Tian

Affiliation: College of Life Science & Bioengineering, Beijing University of Technology, Beijing 100124, China.


The electrochemical synthesis of o-benzoquinones and their in situ transformation is a versatile approach for the synthesis of polyhydroxylated aromatics. In the present paper, the electrochemical oxidation of catechol in the presence of ketene N,S-acetals as N,Cdoubly nucleophiles was first investigated using cyclic voltammetry technique. Then preparative scale of electrolysis was carried out to demonstrate that polyfunctionalized indoles could be one-pot synthesized under constant current electrolysis conditions. Finally, the reaction mechanism was proposed.

Keywords: Anodic oxidation, catechols, ketene N, S-acetals, polyhydroxylated indoles.

Order Reprints Order Eprints Rights & PermissionsPrintExport

Article Details

Page: [141 - 148]
Pages: 8
DOI: 10.2174/1570179411999140304143341