2‐Methyltetrahydrofuran: A Green Solvent for Iron‐Catalyzed Cross‐Coupling Reactions,ChemSusChem

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2‐Methyltetrahydrofuran: A Green Solvent for Iron‐Catalyzed Cross‐Coupling Reactions
ChemSusChem ( IF 7.5 ) Pub Date : 2018-03-26 , DOI: 10.1002/cssc.201800142
Elwira Bisz ₁ , Michal Szostak _{1,

2}

Affiliation

Iron‐catalyzed cross‐coupling reactions allow sustainable formation of C−C bonds using cost‐effective, earth‐abundant base‐metal catalysis for complex syntheses of pharmaceuticals, natural products, and fine chemicals. The major challenge to maintain full sustainability of the process is the identification of green and renewable solvents that can be harnessed to replace the conventional solvents for this highly attractive reaction. Herein, iron‐catalyzed cross‐coupling of aryl chlorides and tosylates with challenging organometallic reagents possessing β‐hydrogens is found to proceed in good to excellent yields with the green, sustainable, and eco‐friendly 2‐methyltetrahydrofuran (2‐MeTHF) as solvent. The reaction operates with excellent functional group tolerance under very mild conditions. Furthermore, large‐scale cross‐coupling, cross‐coupling of heteroaromatic substrates, and cross‐coupling of challenging aryl tosylates and carbamates mediated by Fe–N‐heterocyclic carbene catalytic systems in eco‐friendly 2‐MeTHF were also carried out. The developed method was applied to the key cross‐coupling in the synthesis of a fibrinolysis inhibitor, further highlighting the potential of 2‐MeTHF as a general solvent for sustainable iron‐catalyzed cross‐coupling reactions.

中文翻译：

2-甲基四氢呋喃：铁催化交叉偶联反应的绿色溶剂

铁催化的交叉偶联反应可利用经济高效的，地球上富集的贱金属催化物，用于复杂的药物，天然产物和精细化学品的合成，以可持续方式形成C-C键。维持过程的完全可持续性的主要挑战是鉴定绿色和可再生溶剂，可利用这些溶剂替代传统溶剂以实现这一极具吸引力的反应。本文发现，以绿色，可持续且环保的2-甲基四氢呋喃（2-MeTHF）为溶剂，芳基氯化物和甲苯磺酸盐与具有挑战性的具有β-氢的有机金属试剂进行铁催化的交叉偶联，收率良好。。该反应在非常温和的条件下以优异的官能团耐受性进行。此外，大规模的交叉耦合还进行了杂芳族底物的交叉偶联以及Fe-N-杂环卡宾催化体系介导的具有挑战性的芳基甲苯磺酸盐和氨基甲酸酯在生态友好的2-MeTHF中的交叉偶联。该开发的方法已应用于纤维蛋白溶解抑制剂合成中的关键交叉偶联，进一步凸显了2-MeTHF作为可持续的铁催化交叉偶联反应的一般溶剂的潜力。

更新日期：2018-03-26

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