Synthesis of [2, 2']Bifuranyl‐5, 5'‐dicarboxylic Acid Esters via Reductive Homocoupling of 5‐Bromofuran‐2‐carboxylates Using Alcohols as Reductants†. Issue 1 (7th December 2020)

• Record Type: Journal Article
• Authors: Xie, Yi; Yu, Bin; Luo, Jiajun; Yin, Biaolin; Jiang, Huanfeng
• Is Part Of: Chinese journal of chemistry. Volume 39:Issue 1(2021)
• Page Start: 62
• Page End: 68
• Publication Date: 2020-12-07
• Subjects: Bifuranyl dicarboxylates -- Homocoupling -- Bromination -- Green reductant; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.202000303
• Languages: English
• ISSNs: 1001-604X

Abstract

Abstract : Herein, we describe an environmentally benign and cost‐effective protocol for the synthesis of valuable bifuranyl dicarboxylates, starting with α‐bromination of readily accessible furan‐2‐carboxylates by LiBr and K2 S2 O8 . Furthermore, the bromination intermediate product 5‐bromofuran‐2‐carboxylates were then conducted in a palladium‐catalyzed reductive homocoupling reactions in the presence of alcohols to afford bifuranyl dicarboxylates. One of the final products in this protocol, [2, 2']bifuran‐5, 5'‐dicarboxylic acid esters, are essential monomers of poly(ethylene bifuranoate), which can be served as an green and versatile alternative polymer for traditional poly(ethylene terephthalate) that is currently common in technical plastics. Abstract : We developed an environmentally benign protocol for α‐bromination of furan‐2‐carboxylates with LiBr and K2 S2 O8 in good yields. The resulting 5‐bromofuran‐2‐carboxylates further underwent palladium‐catalyzed reductive homocoupling reactions in alcohols using as reductants to afford [2, 2']bifuran‐5, 5'‐dicarboxylic acid esters as the monomers of promising polymer.