Synergistic Cooperative Effect of L‐Arginine‐[bmim]Br in Cascade Decarboxylative Knoevenagel‐Thia‐Michael Addition Reactions: Green Approach Towards C−S Bond Formation with In Situ Generated Unactivated α,β‐Unsaturated Ester,Advanced Synthesis & Catalysis

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Synergistic Cooperative Effect of L‐Arginine‐[bmim]Br in Cascade Decarboxylative Knoevenagel‐Thia‐Michael Addition Reactions: Green Approach Towards C−S Bond Formation with In Situ Generated Unactivated α,β‐Unsaturated Ester
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-10-12 , DOI: 10.1002/adsc.201801150
Richa Singh ₁ , Yogesh Thopate _{1,

2} , Danish Equbal ₁ , Arun K. Sinha _{1,

2}

Affiliation

In this report, a synergistic combination of L‐arginine and [bmim]Br has been realized for the first time towards step‐economical synthesis of β‐aryl‐β‐sulfanyl esters from aromatic aldehyde, malonate and thiol via cascade thia‐Michael addition reaction on in situ formed unactivated β‐aryl‐α,β‐unsaturated esters (via decarboxylative Knoevenagel reaction) under metal‐and acid/base‐free conditions. Furthermore, the gram scalability and recyclability of the catalytic system (up to 5 cycles) makes our one‐pot two‐step protocol more economically efficient and synthetically attractive for cascade C−C and C−S bond formation than traditional two‐step methods. The synergistic interaction of the catalytic system i. e. L‐arginine with [bmim]Br has been probed by NMR (¹H and ¹³C) studies.

中文翻译：

L-精氨酸-[bmim] Br在级联脱羧Knoevenagel-Thia-Michael加成反应中的协同协同作用：绿色方法实现C-S键形成并原位生成未活化的α，β-不饱和酯

在本报告中，首次实现了L-精氨酸和[bmim] Br的协同结合，从而通过级联噻吩-迈克尔加成反应从芳族醛，丙二酸酯和硫醇逐步经济地合成β-芳基-β-硫烷基酯。在无金属和无酸/无碱条件下原位形成未活化的β-芳基-α，β-不饱和酯的反应（通过脱羧Knoevenagel反应）。此外，催化体系的克级可扩展性和可回收性（最多5个循环）使我们的一锅两步方案比传统的两步方法更经济高效，并且对于级联C-C和C-S键的形成具有综合吸引力。催化系统的协同相互作用 e。带有[bmim] Br的L-精氨酸已通过NMR（¹ H和¹³ C）研究进行了探测。

更新日期：2018-10-12

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