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Application of 1,4-pentanediol as a renewable solvent for copper-catalyzed Ullmann-type coupling reactions
Journal of Organometallic Chemistry ( IF 2.1 ) Pub Date : 2023-12-15 , DOI: 10.1016/j.jorganchem.2023.122976
Csaba Árvai , László T. Mika

It was demonstrated that 1,4-pentanediol as a biomass-originated polar protic solvent could be utilized as an alternative reaction medium for copper-catalyzed Ullmann-type coupling reactions of aryl iodides and various amines under mild conditions. The effect of the copper source, the base, the water, and the γ-valerolactone content of the reaction mixture on the reaction performance was investigated. Eighteen cross-coupling products were isolated with yields of 11–69 %, and high purity (>98 %). Two O-arylated products, 4-phenoxypentan-1-ol and 5-phenoxypentan-2-ol were characterized. The recycling of the solvents after product isolation was also demonstrated. These results represent an example that proves that biomass-derived safer solvents can be utilized in common, industrially important transformations.



中文翻译:

1,4-戊二醇作为铜催化乌尔曼偶联反应的可再生溶剂的应用

结果表明,1,4-戊二醇作为一种生物质来源的极性质子溶剂,可以用作温和条件下铜催化芳基碘化物与各种胺的乌尔曼型偶联反应的替代反应介质。研究了铜源、碱、水和反应混合物中γ-戊内酯含量对反应性能的影响。分离出 18 种交叉偶联产物,收率 11-69%,纯度高 (>98%)。表征了两种O-芳基化产物4-苯氧基戊-1-醇和5-苯氧基戊-2-醇。还演示了产物分离后溶剂的回收。这些结果代表了一个例子,证明生物质衍生的更安全的溶剂可以用于常见的、工业上重要的转化。

更新日期:2023-12-15
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