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

Mengmeng Huang, Jingzhou Tang, Jung Keun Kim, Ming Gong, Jianye Zhang, Yabo Li, Yangjie Wu

Organic & biomolecular chemistry 2022 Aug 17

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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.

Citation

Mengmeng Huang, Jingzhou Tang, Jung Keun Kim, Ming Gong, Jianye Zhang, Yabo Li, Yangjie Wu. A simple approach to C3-ethoxycarbonylmethylation of thiophenes/furans with diethyl bromomalonate. Organic & biomolecular chemistry. 2022 Aug 17;20(32):6459-6463