Issue 32, 2022

A simple approach to C3-ethoxycarbonylmethylation of thiophenes/furans with diethyl bromomalonate

Abstract

A mild and efficient visible-light-induced radical method was developed to produce C3-malonated five-membered heterocycles using 2-substituted thiophenes/furans and diethyl bromomalonate as the starting materials. Various 2-substituted (benzo)thiophenes/furans were suitable for the C3-ethoxycarbonylmethylation. The free radical mechanism was proposed based on the results of control experiments, cyclic voltammetry experiments and luminescence quenching experiments. We suggested that the heteroleptic halogen-bridged iridium(III) dimers might play an important role in this system.

Graphical abstract: A simple approach to C3-ethoxycarbonylmethylation of thiophenes/furans with diethyl bromomalonate

Supplementary files

Article information

Article type
Paper
Submitted
03 May 2022
Accepted
08 Jun 2022
First published
10 Jun 2022

Org. Biomol. Chem., 2022,20, 6459-6463

A simple approach to C3-ethoxycarbonylmethylation of thiophenes/furans with diethyl bromomalonate

M. Huang, J. Tang, J. K. Kim, M. Gong, J. Zhang, Y. Li and Y. Wu, Org. Biomol. Chem., 2022, 20, 6459 DOI: 10.1039/D2OB00835A

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