Synthesis of [2,2’]Bifuranyl‐5,5’‐dicarboxylic Acid Esters via Reductive Homocoupling of 5‐Bromofuran‐2‐carboxylates Using Alcohols as Reductants†,Chinese Journal of Chemistry

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Synthesis of [2,2’]Bifuranyl‐5,5’‐dicarboxylic Acid Esters via Reductive Homocoupling of 5‐Bromofuran‐2‐carboxylates Using Alcohols as Reductants†
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2020-09-15 , DOI: 10.1002/cjoc.202000303
Yi Xie ₁ , Bin Yu ₁ , Jiajun Luo ₁ , Biaolin Yin ₁ , Huanfeng Jiang ₁

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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 K₂S₂O₈. 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.

中文翻译：

使用醇作为还原剂，通过5-溴呋喃-2-羧酸酯的还原均偶联反应合成[2,2']双呋喃基-5,5'-二羧酸酯†

本文中，我们描述了一种环境友好且具有成本效益的方案，用于合成有价值的呋喃二甲酸二羧酸酯，首先是通过LiBr和K ₂ S ₂ O ₈对易得的呋喃-2-羧酸酯进行α-溴化反应。此外，然后在醇存在下，在钯催化的还原均偶联反应中进行溴化中间产物5-溴呋喃-2-羧酸酯的合成，得到双呋喃基二羧酸酯。该协议的最终产品之一，[2,2'] bifuran-5,5'-二羧酸酯是聚（呋喃二甲酸乙二酯）的重要单体，可用作传统聚对苯二甲酸乙二醇酯的绿色多用途替代聚合物。（对苯二甲酸乙二醇酯）目前在工业塑料中很常见。

更新日期：2020-09-15

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