首页 > 最新文献

Tetrahedron最新文献

英文 中文
Recyclable Ag/GO-NH2 catalyzed multicomponent aminophosphinoylation of benzyl alcohols with amines and H-phosphine oxides 可回收 Ag/GO-NH2 与胺和 H-膦氧化物催化苄醇的多组分氨基膦酰化反应
IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC
Tetrahedron
Pub Date : 2024-11-08 DOI: 10.1016/j.tet.2024.134359
Qiang Huang , Lei Zhu , Zhonghua Shi , Xin Jin , Wenwu Zhong
An Ag nanoparticles immobilized heterogeneous composite (Ag/GO-NH2) was synthesized by anchoring nitrogen-containing small molecule onto graphene. The prepared Ag/GO-NH2 was characterized by FT-IR, XRD, SEM and TEM, identifying its structure and composition. Remarkably, the Ag/GO-NH2 composite emerged as a heterogeneous catalyst, they can promote the multi-component aminophosphinoylation of benzyl alcohols with amines and H-phosphine oxides. This heterogeneous catalytic system demonstrated good functional group tolerance and broad substrate scope, affording various α-aminophosphine oxides in good yields. Additionally, the nanocatalyst can be recovered and reused without significant decrease performance of the reaction. It offers an alternative and promising strategy for the heterogeneous synthesis of α-aminophosphine oxides.
通过将含氮小分子锚定在石墨烯上，合成了一种固定银纳米颗粒的异质复合材料（Ag/GO-NH2）。通过傅立叶变换红外光谱（FT-IR）、X射线衍射（XRD）、扫描电镜（SEM）和电子显微镜（TEM）对制备的Ag/GO-NH2进行了表征，确定了其结构和组成。值得注意的是，Ag/GO-NH2 复合材料是一种异相催化剂，它们能促进苄醇与胺和 H-膦氧化物的多组分氨基膦酰化反应。这种异相催化体系具有良好的官能团耐受性和广泛的底物范围，能以良好的产率获得各种α-氨基膦氧化物。此外，这种纳米催化剂可以回收和重复使用，而不会明显降低反应性能。它为α-氨基膦氧化物的异构合成提供了一种可供选择且前景广阔的策略。
{"title":"Recyclable Ag/GO-NH2 catalyzed multicomponent aminophosphinoylation of benzyl alcohols with amines and H-phosphine oxides","authors":"Qiang Huang ,&nbsp;Lei Zhu ,&nbsp;Zhonghua Shi ,&nbsp;Xin Jin ,&nbsp;Wenwu Zhong","doi":"10.1016/j.tet.2024.134359","DOIUrl":"10.1016/j.tet.2024.134359","url":null,"abstract":"<div><div>An Ag nanoparticles immobilized heterogeneous composite (Ag/GO-NH<sub>2</sub>) was synthesized by anchoring nitrogen-containing small molecule onto graphene. The prepared Ag/GO-NH<sub>2</sub> was characterized by FT-IR, XRD, SEM and TEM, identifying its structure and composition. Remarkably, the Ag/GO-NH<sub>2</sub> composite emerged as a heterogeneous catalyst, they can promote the multi-component aminophosphinoylation of benzyl alcohols with amines and H-phosphine oxides. This heterogeneous catalytic system demonstrated good functional group tolerance and broad substrate scope, affording various α-aminophosphine oxides in good yields. Additionally, the nanocatalyst can be recovered and reused without significant decrease performance of the reaction. It offers an alternative and promising strategy for the heterogeneous synthesis of α-aminophosphine oxides.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134359"},"PeriodicalIF":2.1,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657403","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Electrochemical-promoted Mannich-type three-component reaction of benzo-fused cyclic amides using methanol as C1 source instead of formaldehyde 用甲醇代替甲醛作为 C1 源，电化学促进苯并融合环酰胺的曼尼希式三组分反应
IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC
Tetrahedron
Pub Date : 2024-11-08 DOI: 10.1016/j.tet.2024.134357
Yahui Sang , Jinjin Zhang , Mengjia Zhao , Haijuan Qin , Chao Chen , Wei Liu
The three-component N-Mannich reaction is provided in an electrochemical variant. The corresponding N-Mannich base products were obtained by the one-pot method of benzo-fused cyclic amides with secondary amines under a small current of 3 mA using methanol as the carbon source. The reaction is simple to carry out (room temperature and air environment) and requires no supporting electrolytes, using TEMPO as the oxidizing agent. The substrate scope is wide, and the yield is good (39 cases, up to 99 %). CV experiments show that secondary amines are oxidized first at the anode. Moreover, this reaction can be scaled up to the grams.
三组分 N-Mannich 反应以电化学变体的形式出现。以甲醇为碳源，在 3 mA 的小电流下，通过苯并融合环酰胺与仲胺的一锅法获得了相应的 N-Mannich 碱产物。该反应以 TEMPO 为氧化剂，操作简单（室温和空气环境），无需辅助电解质。底物范围广，产率高（39 例，高达 99%）。CV 实验表明，仲胺首先在阳极被氧化。此外，该反应还可以放大到克级。
{"title":"Electrochemical-promoted Mannich-type three-component reaction of benzo-fused cyclic amides using methanol as C1 source instead of formaldehyde","authors":"Yahui Sang ,&nbsp;Jinjin Zhang ,&nbsp;Mengjia Zhao ,&nbsp;Haijuan Qin ,&nbsp;Chao Chen ,&nbsp;Wei Liu","doi":"10.1016/j.tet.2024.134357","DOIUrl":"10.1016/j.tet.2024.134357","url":null,"abstract":"<div><div>The three-component <em>N</em>-Mannich reaction is provided in an electrochemical variant. The corresponding <em>N</em>-Mannich base products were obtained by the one-pot method of benzo-fused cyclic amides with secondary amines under a small current of 3 mA using methanol as the carbon source. The reaction is simple to carry out (room temperature and air environment) and requires no supporting electrolytes, using TEMPO as the oxidizing agent. The substrate scope is wide, and the yield is good (39 cases, up to 99 %). CV experiments show that secondary amines are oxidized first at the anode. Moreover, this reaction can be scaled up to the grams.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134357"},"PeriodicalIF":2.1,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657402","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
An unexpected Michael type addition-deacylpyrazole involving coumarin-3-formylpyrazoles under mild conditions 温和条件下涉及香豆素-3-甲酰基吡唑的意想不到的迈克尔式加成-去酰基吡唑
IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC
Tetrahedron
Pub Date : 2024-11-08 DOI: 10.1016/j.tet.2024.134360
Chuan-Wen Lei , Jiao-Jiao Lei , Xiao-Li Feng , Wen-Hui Zhang , Ze-Gang Ma , You-Ping Tian , Ying Zhou
The first Michael type addition-deacylpyrazole involving α,β-unsaturated pyrazolamides was accomplished by utilizing DMAP as catalyst in mild condition. The protocol enables the access to various oxindole-substituted dihydrocoumarins from coumarin-3-formylpyrazoles and 3-acetoxy oxindoles in excellent yields (up to 99 % yield) with acceptable diastereoselectivities (up to >95:5 dr). In this work, the acylpyrazole group of coumarin-3-formylpyrazoles acted as a temporary activating group for the first time. Detailed mechanistic studies were performed with high resolution mass spectrometry (HRMS) analysis.
利用 DMAP 作为催化剂，在温和条件下首次完成了涉及 α、β-不饱和吡唑酰胺的迈克尔加成-去乙酰基吡唑。该方法可以从香豆素-3-甲酰基吡唑和 3-乙酰氧基氧茚酮中获得各种吲哚取代的二氢香豆素，收率极高（高达 99%），非对映选择性也可以接受（高达 95:5dr）。在这项工作中，香豆素-3-甲酰基吡唑的酰基吡唑基团首次充当了临时活化基团。通过高分辨率质谱分析进行了详细的机理研究。
{"title":"An unexpected Michael type addition-deacylpyrazole involving coumarin-3-formylpyrazoles under mild conditions","authors":"Chuan-Wen Lei ,&nbsp;Jiao-Jiao Lei ,&nbsp;Xiao-Li Feng ,&nbsp;Wen-Hui Zhang ,&nbsp;Ze-Gang Ma ,&nbsp;You-Ping Tian ,&nbsp;Ying Zhou","doi":"10.1016/j.tet.2024.134360","DOIUrl":"10.1016/j.tet.2024.134360","url":null,"abstract":"<div><div>The first Michael type addition-deacylpyrazole involving α,β-unsaturated pyrazolamides was accomplished by utilizing DMAP as catalyst in mild condition. The protocol enables the access to various oxindole-substituted dihydrocoumarins from coumarin-3-formylpyrazoles and 3-acetoxy oxindoles in excellent yields (up to 99 % yield) with acceptable diastereoselectivities (up to &gt;95:5 dr). In this work, the acylpyrazole group of coumarin-3-formylpyrazoles acted as a temporary activating group for the first time. Detailed mechanistic studies were performed with high resolution mass spectrometry (HRMS) analysis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134360"},"PeriodicalIF":2.1,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657306","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A recent update on pallavicinia diterpenoids: Isolation, biogenetic pathway and total synthesis 关于 pallavicinia 二萜类化合物的最新进展：分离、生物遗传途径和全合成
IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC
Tetrahedron
Pub Date : 2024-11-07 DOI: 10.1016/j.tet.2024.134364
Xiwu Zhang, Ru Sun
Pallavicinia diterpenoids are isolated from the genus Pallavicinia of liverworts. Herein, the isolation, biogenetic pathway and total synthesis of pallavicinia diterpenoids with four distinct and complex skeletons were discribed. In this review, all successful total syntheses of 16 pallavicinia diterpenoids were introduced respectively in detail. These outstanding synthetic work will provide more inspiration and pave the stage for ingenious and efficient synthesis of newly discovered pallavicinia diterpenoids as well as other complex natural products, further promoting comprehensive biological evaluation.
Pallavicinia 二萜是从肝草属 Pallavicinia 中分离出来的。本文介绍了具有四种不同和复杂骨架的 Pallavicinia 二萜的分离、生物遗传途径和全合成。在这篇综述中，分别详细介绍了所有成功合成 16 个 pallavicinia 二萜的方法。这些出色的合成工作将为新发现的 pallavicinia 二萜及其他复杂天然产物的巧妙、高效合成提供更多的启发和铺垫，进一步促进全面的生物学评价。
{"title":"A recent update on pallavicinia diterpenoids: Isolation, biogenetic pathway and total synthesis","authors":"Xiwu Zhang,&nbsp;Ru Sun","doi":"10.1016/j.tet.2024.134364","DOIUrl":"10.1016/j.tet.2024.134364","url":null,"abstract":"<div><div><em>Pallavicinia</em> diterpenoids are isolated from the genus <em>Pallavicinia</em> of liverworts. Herein, the isolation, biogenetic pathway and total synthesis of <em>pallavicinia</em> diterpenoids with four distinct and complex skeletons were discribed. In this review, all successful total syntheses of 16 <em>pallavicinia</em> diterpenoids were introduced respectively in detail. These outstanding synthetic work will provide more inspiration and pave the stage for ingenious and efficient synthesis of newly discovered <em>pallavicinia</em> diterpenoids as well as other complex natural products, further promoting comprehensive biological evaluation.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134364"},"PeriodicalIF":2.1,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657407","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
An NAD+ with dually modified adenine for labeling ADP-ribosylation-specific proteins 用于标记 ADP-核糖基化特异性蛋白质的具有双重修饰腺嘌呤的 NAD+。
IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC
Tetrahedron
Pub Date : 2024-11-06 DOI: 10.1016/j.tet.2024.134361
Lei Zhang , Xiao-Nan Zhang , Arshad J. Ansari , Yong Zhang
Protein adenosine diphosphate (ADP)-ribosylation participates in various pivotal cellular events. Its readers and erasers play key roles in modulating ADP-ribosylation-based signaling pathways. Unambiguous assignments of readers and erasers to individual ADP-ribosylated proteins provide insightful knowledge on ADP-ribosylation biology and require the development of tools and technologies for this goal. Herein, we report the design and the synthesis of a nicotinamide adenine dinucleotide (NAD+) carrying a photoactive and a clickable group. Functioning as a substrate for poly-ADP-ribosylation (PARylation), this NAD+ mimic with dually modified adenine enables covalent crosslinking and labeling of proteins bound to PARylation, representing a new photoaffinity probe for studying this critical post-translational modification.
蛋白质二磷酸腺苷（ADP）-核糖基化参与了各种关键的细胞事件。其阅读器和清除器在调节基于 ADP 核糖基化的信号通路中发挥着关键作用。为单个 ADP 核糖基化蛋白质明确分配读取器和清除器可提供有关 ADP 核糖基化生物学的深刻知识，并需要为此开发工具和技术。在此，我们报告了一种携带光活性基团和可点击基团的烟酰胺腺嘌呤二核苷酸（NAD+）的设计与合成。作为多-ADP-核糖基化（PARylation）的底物，这种具有双重修饰腺嘌呤的 NAD+ 模拟物能使与 PARylation 结合的蛋白质发生共价交联和标记，是研究这种关键的翻译后修饰的一种新的光亲和探针。
{"title":"An NAD+ with dually modified adenine for labeling ADP-ribosylation-specific proteins","authors":"Lei Zhang ,&nbsp;Xiao-Nan Zhang ,&nbsp;Arshad J. Ansari ,&nbsp;Yong Zhang","doi":"10.1016/j.tet.2024.134361","DOIUrl":"10.1016/j.tet.2024.134361","url":null,"abstract":"<div><div>Protein adenosine diphosphate (ADP)-ribosylation participates in various pivotal cellular events. Its readers and erasers play key roles in modulating ADP-ribosylation-based signaling pathways. Unambiguous assignments of readers and erasers to individual ADP-ribosylated proteins provide insightful knowledge on ADP-ribosylation biology and require the development of tools and technologies for this goal. Herein, we report the design and the synthesis of a nicotinamide adenine dinucleotide (NAD<sup>+</sup>) carrying a photoactive and a clickable group. Functioning as a substrate for poly-ADP-ribosylation (PARylation), this NAD<sup>+</sup> mimic with dually modified adenine enables covalent crosslinking and labeling of proteins bound to PARylation, representing a new photoaffinity probe for studying this critical post-translational modification.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134361"},"PeriodicalIF":2.1,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142646723","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chemical synthesis of 13C-labeled isopentenyl pyrophosphate 13C 标记的焦磷酸异戊烯酯的化学合成
IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC
Tetrahedron
Pub Date : 2024-11-04 DOI: 10.1016/j.tet.2024.134356
Ruoyao Liu , Zhiyuan Ren , Zixin Deng , Min Xu , Anwei Hou
Isopentenyl pyrophosphate (IPP) is a key precursor in the biosynthesis of terpenoids, the largest class of natural products. 13C isotope incorporation into the terpenoid scaffolds has been proved to be a powerful chemical probe to track the elusive cyclization mechanism of distinct terpene synthases which are the driving force for the tremendous chemical diversities seen in terpenoid natural products. Here, we present synthetic routes for the preparation of C1 to C5 individually 13C labeled IPP starting from 13C-labeled acetic acid and iodomethane, resulting in five distinct labeled substrates. The 13C labeled IPP will be served as useful chemical probes to elucidate the new cyclization mechanisms catalyzed by those cryptic terpene synthases.
焦磷酸异戊烯酯（IPP）是最大一类天然产品--萜类化合物生物合成过程中的关键前体。13C 同位素掺入萜类化合物支架已被证明是一种强大的化学探针，可用于追踪不同萜类化合物合成酶难以捉摸的环化机制，而萜类化合物合成酶是萜类天然产物化学多样性的驱动力。在这里，我们介绍了从 13C 标记乙酸和碘甲烷开始制备 C1 到 C5 单独 13C 标记 IPP 的合成路线，从而得到五种不同的标记底物。13C 标记的 IPP 将作为有用的化学探针，用于阐明这些隐性萜烯合成酶催化的新环化机制。
{"title":"Chemical synthesis of 13C-labeled isopentenyl pyrophosphate","authors":"Ruoyao Liu ,&nbsp;Zhiyuan Ren ,&nbsp;Zixin Deng ,&nbsp;Min Xu ,&nbsp;Anwei Hou","doi":"10.1016/j.tet.2024.134356","DOIUrl":"10.1016/j.tet.2024.134356","url":null,"abstract":"<div><div>Isopentenyl pyrophosphate (IPP) is a key precursor in the biosynthesis of terpenoids, the largest class of natural products. <sup>13</sup>C isotope incorporation into the terpenoid scaffolds has been proved to be a powerful chemical probe to track the elusive cyclization mechanism of distinct terpene synthases which are the driving force for the tremendous chemical diversities seen in terpenoid natural products. Here, we present synthetic routes for the preparation of C1 to C5 individually <sup>13</sup>C labeled IPP starting from <sup>13</sup>C-labeled acetic acid and iodomethane, resulting in five distinct labeled substrates. The <sup>13</sup>C labeled IPP will be served as useful chemical probes to elucidate the new cyclization mechanisms catalyzed by those cryptic terpene synthases.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134356"},"PeriodicalIF":2.1,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142654177","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of 1,3,5-trisubstituted 1,2,4-triazoles enabled by a gold-catalyzed three-component reaction 通过金催化的三组分反应合成 1,3,5-三取代的 1,2,4-三唑
IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC
Tetrahedron
Pub Date : 2024-11-03 DOI: 10.1016/j.tet.2024.134358
Howard Díaz-Salazar, Carlos M. Ramírez-González, Miguel A. Rosas-Ortega, Susana Porcel
Valuable fully substituted 1,2,4-triazoles are obtained via a gold-catalyzed three-component reaction involving ethyl diazoacetate, aryldiazonium salts, and nitriles. The reaction proceeds under mild conditions, is regioselective, and allows the introduction of mono- and di-substituted aryl rings at the ortho, meta, and para positions. Mechanistic evidence suggests the participation of Au(III) species as the active catalysts.
通过金催化的重氮乙酸乙酯、芳基重氮盐和腈的三组分反应，获得了有价值的全取代 1,2,4 三唑。该反应在温和的条件下进行，具有区域选择性，可在正位、偏位和对位引入单取代和二取代芳基环。机理证据表明，Au(III) 物种是活性催化剂。
{"title":"Synthesis of 1,3,5-trisubstituted 1,2,4-triazoles enabled by a gold-catalyzed three-component reaction","authors":"Howard Díaz-Salazar,&nbsp;Carlos M. Ramírez-González,&nbsp;Miguel A. Rosas-Ortega,&nbsp;Susana Porcel","doi":"10.1016/j.tet.2024.134358","DOIUrl":"10.1016/j.tet.2024.134358","url":null,"abstract":"<div><div>Valuable fully substituted 1,2,4-triazoles are obtained via a gold-catalyzed three-component reaction involving ethyl diazoacetate, aryldiazonium salts, and nitriles. The reaction proceeds under mild conditions, is regioselective, and allows the introduction of mono- and di-substituted aryl rings at the <em>ortho</em>, <em>meta,</em> and <em>para</em> positions. Mechanistic evidence suggests the participation of Au(III) species as the active catalysts.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134358"},"PeriodicalIF":2.1,"publicationDate":"2024-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142592708","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Transition-metal-free nucleophilic substitution of alkenyl boronic acids with propargylic mesylates sp3-carbon electrophiles 烯基硼酸与丙炔基甲磺酸酯 sp3 碳亲电体的无过渡金属亲核取代反应
IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC
Tetrahedron
Pub Date : 2024-11-02 DOI: 10.1016/j.tet.2024.134353
Wenna Xie , Shiwen Liu , Bo Xu
We developed a highly versatile transition metal-free Suzuki type cross-coupling protocol. Alkenyl/aryl boronic acids could couple smoothly with propargylic mesylates Csp3 electrophiles in the presence of mild bases. The counterion in the base plays a crucial role for the reactivity. Our metal-free condition is orthogonal towards the classic transition metal catalysed Suzuki reactions.
我们开发了一种用途广泛的无过渡金属铃木型交叉偶联方案。在温和的碱存在下，烯基/芳基硼酸能与丙炔基甲磺酸酯 Csp3 亲电体顺利偶联。碱中的反离子对反应活性起着至关重要的作用。我们的无金属条件与经典的过渡金属催化的铃木反应是正交的。
{"title":"Transition-metal-free nucleophilic substitution of alkenyl boronic acids with propargylic mesylates sp3-carbon electrophiles","authors":"Wenna Xie ,&nbsp;Shiwen Liu ,&nbsp;Bo Xu","doi":"10.1016/j.tet.2024.134353","DOIUrl":"10.1016/j.tet.2024.134353","url":null,"abstract":"<div><div>We developed a highly versatile transition metal-free Suzuki type cross-coupling protocol. Alkenyl/aryl boronic acids could couple smoothly with propargylic mesylates Csp3 electrophiles in the presence of mild bases. The counterion in the base plays a crucial role for the reactivity. Our metal-free condition is orthogonal towards the classic transition metal catalysed Suzuki reactions.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134353"},"PeriodicalIF":2.1,"publicationDate":"2024-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142587327","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Enhancing stability of cationic palladium complexes with hemilabile 2-benzyl oxazoline ligands: Structural insights and catalytic implications 增强具有半亲和 2-苄基噁唑啉配体的阳离子钯配合物的稳定性：结构见解和催化影响
IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC
Tetrahedron
Pub Date : 2024-11-02 DOI: 10.1016/j.tet.2024.134348
Guldana Issabayeva , On-Yu Kang , Hyojung Ahn , Seong Jun Park , Hwan Jung Lim
This article describes the synthesis and characterization of Pd cationic complexes incorporating mono(2-benzyl oxazoline) ligands. Our study focuses on exploring the impact of electrostatic interactions of aromatic π-electrons of the benzyl group, aimed at enhancing the structural rigidity of cationic Pd complexes. Introduction of an aromatic moiety, which weakly coordinates with the Pd cation, led to a two-fold increase in the stability of the Pd cationic complex compared to complexes lacking any coordinating substituents. This research represents the initial instance of a cationic Pd complex with 2-benzyl oxazolines, highlighting the importance of weak electrostatic interactions in elucidating the three-dimensional structure of a metal complex.
本文介绍了含有单（2-苄基噁唑啉）配体的钯阳离子配合物的合成和表征。我们的研究重点是探索苄基芳香族 π 电子的静电相互作用的影响，旨在增强阳离子钯配合物的结构刚性。引入一个与钯阳离子弱配位的芳香基团后，钯阳离子络合物的稳定性比没有任何配位取代基的络合物提高了两倍。这项研究是 2-苄基恶唑啉阳离子钯配合物的首次实例，突出了弱静电相互作用在阐明金属配合物三维结构方面的重要性。
{"title":"Enhancing stability of cationic palladium complexes with hemilabile 2-benzyl oxazoline ligands: Structural insights and catalytic implications","authors":"Guldana Issabayeva ,&nbsp;On-Yu Kang ,&nbsp;Hyojung Ahn ,&nbsp;Seong Jun Park ,&nbsp;Hwan Jung Lim","doi":"10.1016/j.tet.2024.134348","DOIUrl":"10.1016/j.tet.2024.134348","url":null,"abstract":"<div><div>This article describes the synthesis and characterization of Pd cationic complexes incorporating mono(2-benzyl oxazoline) ligands. Our study focuses on exploring the impact of electrostatic interactions of aromatic π-electrons of the benzyl group, aimed at enhancing the structural rigidity of cationic Pd complexes. Introduction of an aromatic moiety, which weakly coordinates with the Pd cation, led to a two-fold increase in the stability of the Pd cationic complex compared to complexes lacking any coordinating substituents. This research represents the initial instance of a cationic Pd complex with 2-benzyl oxazolines, highlighting the importance of weak electrostatic interactions in elucidating the three-dimensional structure of a metal complex.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134348"},"PeriodicalIF":2.1,"publicationDate":"2024-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142654178","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Gold(III)-catalyzed regioselective synthesis of vinyl-substituted pyrazolo[1,4]-oxazepines via 7-exo-trig cyclization 金(III)催化的乙烯基取代的吡唑并[1,4]氮杂卓通过 7-exo-trig 环化的区域选择性合成
IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC
Tetrahedron
Pub Date : 2024-11-02 DOI: 10.1016/j.tet.2024.134340
Ravinder Guduru , Mathangi Sandeep , Komalla Sunil , N.S.V.M. Rao Mangina , Perla Bharath Kumar , Balasubramanian Sridhar , Galla V. Karunakar
Vinyl-substituted pyrazo[1,4]-oxazepines were prepared through an intramolecular regioselective cyclization method under gold catalysis. This organic transformation achieved selective C–N bond formation via 7-exo-trig cyclization, resulting in vinyl-containg pyrazolo[1,4]-benzooxazepines and pyrazolo[1,4]-naphthoxazepines in one-pot with moderate to very good yields.
在金催化下，通过分子内区域选择性环化方法制备了乙烯基取代的吡唑并[1,4]-氧氮杂卓。这种有机转化通过 7-exo-trig 环化实现了选择性 C-N 键的形成，从而以中等至非常好的收率，在一锅中制备出乙烯基构象的吡唑并[1,4]-苯并氧氮杂卓和吡唑并[1,4]-萘并氧氮杂卓。
{"title":"Gold(III)-catalyzed regioselective synthesis of vinyl-substituted pyrazolo[1,4]-oxazepines via 7-exo-trig cyclization","authors":"Ravinder Guduru ,&nbsp;Mathangi Sandeep ,&nbsp;Komalla Sunil ,&nbsp;N.S.V.M. Rao Mangina ,&nbsp;Perla Bharath Kumar ,&nbsp;Balasubramanian Sridhar ,&nbsp;Galla V. Karunakar","doi":"10.1016/j.tet.2024.134340","DOIUrl":"10.1016/j.tet.2024.134340","url":null,"abstract":"<div><div>Vinyl-substituted pyrazo[1,4]-oxazepines were prepared through an intramolecular regioselective cyclization method under gold catalysis. This organic transformation achieved selective C–N bond formation <em>via 7-exo-trig</em> cyclization, resulting in vinyl-containg pyrazolo[1,4]-benzooxazepines and pyrazolo[1,4]-naphthoxazepines in one-pot with moderate to very good yields.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134340"},"PeriodicalIF":2.1,"publicationDate":"2024-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142592623","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
首页 上一页 下一页 尾页
类型
全部 化学•材料 生命科学 医学 物理 工程技术 环境•农林 材料科学 地球科学 法学 管理学 化学 环境科学与生态学 计算机科学 教育学 经济学 农林科学 人文科学 生物学 数学 物理与天体物理 心理学 综合性期刊 其他 工业工程 理学 历史学 农学 文学 信息工程
数据库
全部 ACS Publications Elsevier ieeexplore Springer The Royal Society of Chemistry Wiley
期刊
Tetrahedron
全部 Acc. Chem. Res. ACS Applied Bio Materials ACS Appl. Electron. Mater. ACS Appl. Energy Mater. ACS Appl. Mater. Interfaces ACS Appl. Nano Mater. ACS Appl. Polym. Mater. ACS BIOMATER-SCI ENG ACS Catal. ACS Cent. Sci. ACS Chem. Biol. ACS Chemical Health & Safety ACS Chem. Neurosci. ACS Comb. Sci. ACS Earth Space Chem. ACS Energy Lett. ACS Infect. Dis. ACS Macro Lett. ACS Mater. Lett. ACS Med. Chem. Lett. ACS Nano ACS Omega ACS Photonics ACS Sens. ACS Sustainable Chem. Eng. ACS Synth. Biol. Anal. Chem. BIOCHEMISTRY-US Bioconjugate Chem. BIOMACROMOLECULES Chem. Res. Toxicol. Chem. Rev. Chem. Mater. CRYST GROWTH DES ENERG FUEL Environ. Sci. Technol. Environ. Sci. Technol. Lett. Eur. J. Inorg. Chem. IND ENG CHEM RES Inorg. Chem. J. Agric. Food. Chem. J. Chem. Eng. Data J. Chem. Educ. J. Chem. Inf. Model. J. Chem. Theory Comput. J. Med. Chem. J. Nat. Prod. J PROTEOME RES J. Am. Chem. Soc. LANGMUIR MACROMOLECULES Mol. Pharmaceutics Nano Lett. Org. Lett. ORG PROCESS RES DEV ORGANOMETALLICS J. Org. Chem. J. Phys. Chem. J. Phys. Chem. A J. Phys. Chem. B J. Phys. Chem. C J. Phys. Chem. Lett. Analyst Anal. Methods Biomater. Sci. Catal. Sci. Technol. Chem. Commun. Chem. Soc. Rev. CHEM EDUC RES PRACT CRYSTENGCOMM Dalton Trans. Energy Environ. Sci. ENVIRON SCI-NANO ENVIRON SCI-PROC IMP ENVIRON SCI-WAT RES Faraday Discuss. Food Funct. Green Chem. Inorg. Chem. Front. Integr. Biol. J. Anal. At. Spectrom. J. Mater. Chem. A J. Mater. Chem. B J. Mater. Chem. C Lab Chip Mater. Chem. Front. Mater. Horiz. MEDCHEMCOMM Metallomics Mol. Biosyst. Mol. Syst. Des. Eng. Nanoscale Nanoscale Horiz. Nat. Prod. Rep. New J. Chem. Org. Biomol. Chem. Org. Chem. Front. PHOTOCH PHOTOBIO SCI PCCP Polym. Chem.
﹀
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
×
提示
您的信息不完整，为了账户安全，请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号：481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们：info@booksci.cn
Book学术提供免费学术资源搜索服务，方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1