A simple approach to C3-ethoxycarbonylmethylation of thiophenes/furans with diethyl bromomalonate. Issue 32 (27th July 2022)

• Record Type: Journal Article
• Authors: Huang, Mengmeng; Tang, Jingzhou; Kim, Jung Keun; Gong, Ming; Zhang, Jianye; Li, Yabo; Wu, Yangjie
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 32(2022)
• Page Start: 6459
• Page End: 6463
• Publication Date: 2022-07-27
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00835a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A mild method to produce C3-malonated products was developed via a visible-light-induced radical reaction of 2-substituted 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.