Electrochemical Synthesis of Polyfunctionalized Indoles in Aqueous Medium from Catechols and Ketene N,S-acetals
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.
Keywords: Anodic oxidation, catechols, ketene N, S-acetals, polyhydroxylated indoles.
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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