Issue 8, 2020

Visible-light-induced photocatalyst-free C-3 functionalization of indoles with diethyl bromomalonate

Abstract

A visible-light induced green and efficient method is developed for the synthesis of α-indolyl diethyl malonates. The reaction proceeds without any photocatalysts or ligands in a green solvent in a short time. Moreover, the reaction mechanism has been clearly studied by control experiments, spectrophotometric studies and density functional theory (DFT) calculations. The results showed that the photocatalyst-free transformation may proceed via an XB-promoted radical process. The EDA complex formation of diethyl bromomalonate with a base is the main reason for the reaction initiation.

Graphical abstract: Visible-light-induced photocatalyst-free C-3 functionalization of indoles with diethyl bromomalonate

Supplementary files

Article information

Article type
Paper
Submitted
23 Jan 2020
Accepted
18 Mar 2020
First published
19 Mar 2020

Green Chem., 2020,22, 2543-2548

Visible-light-induced photocatalyst-free C-3 functionalization of indoles with diethyl bromomalonate

G. Gu, M. Huang, J. K. Kim, J. Zhang, Y. Li and Y. Wu, Green Chem., 2020, 22, 2543 DOI: 10.1039/D0GC00292E

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