Exploring Green Solvents Associated to Pd/C as Heterogeneous Catalyst for Direct Arylation of Heteroaromatics with Aryl Bromides,Advanced Synthesis & Catalysis

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Exploring Green Solvents Associated to Pd/C as Heterogeneous Catalyst for Direct Arylation of Heteroaromatics with Aryl Bromides
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-07-06 , DOI: 10.1002/adsc.201800596
Shuxin Mao ₁ , Xinzhe Shi ₁ , Jean-François Soulé ₁ , Henri Doucet ₁

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Metal residues are certainly one of the major sources of contamination of products in metal‐catalyzed direct arylation reactions. We found that the use of only 1 mol% of the heterogeneous catalyst Pd/C promotes very efficiently the direct arylations of most heteroaromatics. In the presence of this catalyst and potassium acetate as the base, the direct arylation of thiophenes, furans, pyrroles, thiazoles, imidazoles or isoxazoles, using aryl bromides as coupling partners, proceeds highly regioselectively and in moderate to very high yields. With several heteroarenes both electron‐deficient and electron‐rich aryl bromides were tolerated; moreover, with the most reactive heteroarenes, the Pd/C catalyst tolerated green solvents such as diethyl carbonate, 3‐methylbutan‐1‐ol and pentan‐1‐ol, affording a synthetic scheme with low environmental impact.

中文翻译：

探索与Pd / C相关的绿色溶剂，作为异芳烃直接催化芳基芳烃与芳基溴化物的芳基化反应

在金属催化的直接芳基化反应中，金属残留物无疑是产品污染的主要来源之一。我们发现仅使用1mol％的多相催化剂Pd / C非常有效地促进了大多数杂芳族化合物的直接芳基化。在该催化剂和乙酸钾为碱的存在下，使用芳基溴化物作为偶联伙伴，噻吩，呋喃，吡咯，噻唑，咪唑或异恶唑的直接芳基化在区域上具有高度选择性，并且产率中等至很高。有了几个杂芳烃，既可以耐受缺电子也可以耐受富电子的芳基溴。此外，对于最具活性的杂芳烃，Pd / C催化剂可耐受绿色溶剂，例如碳酸二乙酯，3-甲基丁烷-1-醇和戊烷-1-醇，从而提供了对环境影响小的合成方案。

更新日期：2018-07-06

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