One-pot synthesis of hydrazono-sulfonamide adducts using Cu(BTC) MOF catalyst and their remarkable AIEE properties: unprecedented copper(II)-catalyzed generation of ketenimine

Mahendran Vaithiyanathan; Shanmugam Sivakumar

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One-pot synthesis of hydrazono-sulfonamide adducts using Cu(BTC) MOF catalyst and their remarkable AIEE properties: unprecedented copper(II)-catalyzed generation of ketenimine

机译：使用Cu（BTC）MOF催化剂的肼 - 磺酰胺加合物的一罐合成及其显着性AIEE特性：前所未有的铜（II） - 催化作用酮亚胺

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An efficient, four-component reaction for the synthesis of hydrazono-sulfonamide adducts via in situ generated ketenimine was discovered. Highly porous copper benzenetricarboxylate [Cu(BTC)], a metal-organic framework (MOF), was used as a heterogeneous catalyst for the four-component coupling reaction involving aldehyde, alkyne, tosyl azide, and phenylhydrazine in a one pot process. For the first time, a copper(II) catalyst was utilized to generate a ketenimine intermediate. The Cu(BTC) catalyst was recycled and reused six times without any substantial loss in the yield. In addition, pyrene adduct (5r) shows remarkable aggregation induced emission enhancement (AIEE) properties, and was studied in detail using THF : water solvent mixtures. Adduct 5r is almost non-emissive in pure THF solution, however, it emits a greenish-yellow colour in the aggregated state. Formation of nano-aggregates was confirmed by TEM analysis. A theoretical DFT study supports the observed photophysical changes.

机译：发现了通过原位产生的酮亚胺合成肼 - 磺酰胺加合物的有效的四分组分反应。高度多孔铜苯甲酸甲酯[Cu（BTC）]，金属 - 有机框架（MOF）用作涉及醛，炔烃，甲酰胺和苯基肼的四组分偶联反应的非均相催化剂。首次，利用铜（II）催化剂产生酮亚胺中间体。将Cu（BTC）催化剂再循环并重复使用六次，而不会在产率下进行大量损失。此外，芘加合物（5R）显示出显着的聚集诱导的发射增强（AIEE）性质，并使用THF进行详细研究：水溶剂混合物。加合物5R在纯THF溶液中几乎是非发光，然而，它在聚合状态下发出绿色黄色。通过TEM分析证实了纳米聚集体的形成。理论DFT研究支持观察到的光物理变化。

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《RSC Advances》 |2015年第26期|共8页
作者
Mahendran Vaithiyanathan; Shanmugam Sivakumar;
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Madurai Kamaraj Univ Sch Chem Dept Organ Chem Madurai 625021 Tamil Nadu India;

Madurai Kamaraj Univ Sch Chem Dept Organ Chem Madurai 625021 Tamil Nadu India;

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正文语种 eng
中图分类化学;
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1. One-pot synthesis of hydrazono-sulfonamide adducts using Cu(BTC) MOF catalyst and their remarkable AIEE properties: unprecedented copper(II)-catalyzed generation of ketenimine [J] . Mahendran Vaithiyanathan, Shanmugam Sivakumar RSC Advances . 2015,第26期

机译：使用Cu（BTC）MOF催化剂的肼 - 磺酰胺加合物的一罐合成及其显着性AIEE特性：前所未有的铜（II） - 催化作用酮亚胺
2. Copper-catalyzed oxidative coupling of arylboronic acids with aryl carboxylic acids: Cu-3(BTC)(2) MOF as a sustainable catalyst to access aryl esters [J] . Devarajan Nainamalai, Suresh Palaniswamy Organic Chemistry Frontiers . 2018,第15期

机译：芳基羧酸芳基硼酸的铜催化氧化偶联：Cu-3（BTC）（2）MOF作为可持续催化剂以进入芳基酯
3. Copper catalyzed oxidative homocoupling of terminal alkynes to 1,3-diynes: A Cu_3(BTC)_2 MOF as an efficient and ligand free catalyst for Glaser-Hay coupling [J] . Devarajan Nainamalai, Karthik Murugan Selvaraj, Suresh Palaniswamy Organic & biomolecular chemistry . 2017,第43期

机译：铜催化端炔与1,3-二炔的氧化均偶联：Cu_3（BTC）_2 MOF作为Glaser-Hay偶联的有效且无配体的催化剂
4. Copper(II) Triflate as a Double Catalyst for the One-Pot Click Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Benzylic Acetates [C] . Eiji Shimizu, Satoshi Kikuchi, Shin-ichi Fnkuzawa Symposium on Organometallic Chemistry . 2007

机译：铜（II）作为单罐的双催化剂，单击1,4-二取代的1,2,3-三唑的双催化剂，从苄基乙酸盐中键合
5. I. Multicatalysis: Development of a Bismuth(III) triflate-catalyzed Nucleophilic addition/ Hydrofunctionalization Reaction in the Synthesis of Complex Heterocycles II. C--H Arylation of Arenes and Heteroarenes with Palladium-Carboxylate Catalysts: Identification of the Catalyst Resting State and the Crucial Role of Pivalate Ligand in Stabilization of the Catalyst III. C--H Arylation of Heteroarenes with Palladium-Carboxylate Catalysts: Importance of Phosphine Ligand for Basic Heteroarene Substrates IV. C--H Arylation of Heteroarenes with Palladium-Carboxylate Catalysts: Effect of the Properties of Basic Heteroarene Substrates on Direct Arylations. [D] . Tundel, Rachel E. 2011

机译：I.多催化作用：在复杂的杂环化合物的合成中三氟甲磺酸铋（III）催化的亲核加成/加氢官能化反应的发展。羰基钯催化剂对芳烃和杂芳烃的CH-H芳基化反应：催化剂静止状态的鉴定以及新戊酸酯配体在稳定催化剂中的关键作用III。羰基钯催化剂催化杂芳烃的CH芳基化：膦配体对基础杂芳烃基质的重要性IV。杂芳烃与钯-羧酸酯的CH芳基化：碱性杂芳烃底物性能对直接芳基化的影响。
6. Corrigendum: Green and Facile Synthesis of Metal-Organic Framework Cu-BTC-Supported Sn (II)-Substituted Keggin Heteropoly Composites as an Esterification Nanocatalyst for Biodiesel Production [O] . Qiuyun Zhang, Dan Ling, Dandan Lei, 2020

机译：勘误：绿色有机合成铜-BTC负载的Sn（II）取代的Keggin杂多复合材料作为生物柴油生产的酯化纳米催化剂
7. Simultaneous introduction of various palladium active sites into MOF via one-pot synthesis: Pd@Cu3−xPdx(BTC)2n [O] . Wenhua Zhang, Zhihao Chen, Majd Al-Naji, 2016

机译：通过单罐合成同时将各种钯活性位点引入MOF中：PD @ CU3-XPDX（BTC）2 n

One-pot synthesis of hydrazono-sulfonamide adducts using Cu(BTC) MOF catalyst and their remarkable AIEE properties: unprecedented copper(II)-catalyzed generation of ketenimine

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