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KOtBu‐Catalyzed Michael Addition Reactions Under Mild and Solvent‐Free Conditions
Chemistry - An Asian Journal ( IF 4.1 ) Pub Date : 2020-01-20 , DOI: 10.1002/asia.201901647
Subramanian Thiyagarajan 1 , Varadhan Krishnakumar 1 , Chidambaram Gunanathan 1
Affiliation  

Designed transition metal complexes predominantly catalyze Michael addition reactions. Inorganic and organic base‐catalyzed Michael addition reactions have been reported. However, known base‐catalyzed reactions suffer from the requirement of solvents, additives, high pressure and also side‐reactions. Herein, we demonstrate a mild and environmentally friendly strategy of readily available KOtBu‐catalyzed Michael addition reactions. This simple inorganic base efficiently catalyzes the Michael addition of underexplored acrylonitriles, esters and amides with (oxa‐, aza‐, and thia‐) heteroatom nucleophiles. This catalytic process proceeds under solvent‐free conditions and at room temperature. Notably, this protocol offers an easy operational procedure, broad substrate scope with excellent selectivity, reaction scalability and excellent TON (>9900). Preliminary mechanistic studies revealed that the reaction follows an ionic mechanism. Formal synthesis of promazine is demonstrated using this catalytic protocol.

中文翻译:

温和无溶剂条件下KOtBu催化的Michael加成反应

设计的过渡金属络合物主要催化迈克尔加成反应。无机和有机碱催化的迈克尔加成反应已有报道。但是,已知的碱催化反应需要溶剂,添加剂,高压以及副反应。在此,我们展示了一种易于使用的KO t的温和且环保的策略Bu催化Michael加成反应。这种简单的无机碱可有效催化未开发的丙烯腈,酯和酰胺与(氧杂,氮杂和硫杂)杂原子亲核试剂的迈克尔加成反应。该催化过程在无溶剂条件和室温下进行。值得注意的是,该协议提供了一种简便的操作程序,宽泛的底物范围,出色的选择性,反应可扩展性和出色的TON(> 9900)。初步的机理研究表明,该反应遵循离子机理。使用该催化方案证明了丙嗪的正式合成。
更新日期:2020-01-21
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