Abstract
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.
Current Organic Synthesis
Title:Electrochemical Synthesis of Polyfunctionalized Indoles in Aqueous Medium from Catechols and Ketene N,S-acetals
Volume: 11 Issue: 1
Author(s): Xiao-Guang Gao, Ni-Tao Zhanga, Cheng-Chu Zeng, Yong-Dong Liu, Li-Ming Hu and Hong-Yu Tian
Affiliation:
Keywords: Anodic oxidation, catechols, ketene N, S-acetals, polyhydroxylated indoles.
Abstract: 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.
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Cite this article as:
Gao Xiao-Guang, Zhanga Ni-Tao, Zeng Cheng-Chu, Liu Yong-Dong, Hu Li-Ming and Tian Hong-Yu, Electrochemical Synthesis of Polyfunctionalized Indoles in Aqueous Medium from Catechols and Ketene N,S-acetals, Current Organic Synthesis 2014; 11 (1) . https://dx.doi.org/10.2174/1570179411999140304143341
DOI https://dx.doi.org/10.2174/1570179411999140304143341 |
Print ISSN 1570-1794 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6271 |
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