NNN pincer palladium(II) complexes with N-(2-(1H-pyrazol-1-yl)phenyl)-picolinamide ligands: synthesis, characterization, and application to heck coupling reaction

IF 1.6 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR
Yongli Xu, Tao Wang, Yonghua Li, Shuxiao Li, Yifan Zhang, Jiaming Wang, Fei Li, Heng Jiang
{"title":"NNN pincer palladium(II) complexes with N-(2-(1H-pyrazol-1-yl)phenyl)-picolinamide ligands: synthesis, characterization, and application to heck coupling reaction","authors":"Yongli Xu,&nbsp;Tao Wang,&nbsp;Yonghua Li,&nbsp;Shuxiao Li,&nbsp;Yifan Zhang,&nbsp;Jiaming Wang,&nbsp;Fei Li,&nbsp;Heng Jiang","doi":"10.1007/s11243-023-00570-7","DOIUrl":null,"url":null,"abstract":"<div><p><i>N</i>-(2-(1H-pyrazol-1-yl)phenyl)-picolinamide ligands <b>3a–c</b> and <b>5a–f</b> have been easily prepared from commercially available 2-pyridinecarboxylic acid. Reaction of <b>3a–c</b> and <b>5a–f</b> with PdCl<sub>2</sub> in toluene in the presence of triethylamine gave the nine NNN pincer Pd(II) complexes <b>6a–i</b> in 15–91% yields. All the new compounds were characterized by <sup>1</sup>H, <sup>13</sup>C NMR spectra and HRMS. In addition, the molecular structures of complexes <b>6a</b> and <b>6i</b> have also been determined by single-crystal X-ray diffraction. The obtained palladium(II) catalysts showed efficient catalytic activity toward the Heck coupling of aryl bromides with styrenes. Under the condition of 5% catalyst loading, the expected various styrenes were obtained in moderate to high yields (up to 99% yield).</p></div>","PeriodicalId":803,"journal":{"name":"Transition Metal Chemistry","volume":"49 3","pages":"149 - 159"},"PeriodicalIF":1.6000,"publicationDate":"2024-01-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Transition Metal Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11243-023-00570-7","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
引用次数: 0

Abstract

N-(2-(1H-pyrazol-1-yl)phenyl)-picolinamide ligands 3a–c and 5a–f have been easily prepared from commercially available 2-pyridinecarboxylic acid. Reaction of 3a–c and 5a–f with PdCl2 in toluene in the presence of triethylamine gave the nine NNN pincer Pd(II) complexes 6a–i in 15–91% yields. All the new compounds were characterized by 1H, 13C NMR spectra and HRMS. In addition, the molecular structures of complexes 6a and 6i have also been determined by single-crystal X-ray diffraction. The obtained palladium(II) catalysts showed efficient catalytic activity toward the Heck coupling of aryl bromides with styrenes. Under the condition of 5% catalyst loading, the expected various styrenes were obtained in moderate to high yields (up to 99% yield).

Abstract Image

具有 N-(2-(1H-吡唑-1-基)苯基)-吡啶醯胺配体的 NNN 夹钯(II)配合物:合成、表征及在偶联反应中的应用
N-(2-(1H-吡唑-1-基)苯基)-吡啶酰胺配体 3a-c 和 5a-f 很容易从市售的 2-吡啶甲酸中制备出来。在三乙胺存在下,3a-c 和 5a-f 与 PdCl2 在甲苯中反应,得到九种 NNN 夹 Pd(II) 复合物 6a-i,产率为 15-91%。所有新化合物都通过 1H、13C NMR 光谱和 HRMS 进行了表征。此外,还通过单晶 X 射线衍射测定了 6a 和 6i 复合物的分子结构。所获得的钯(II)催化剂对芳基溴与苯乙烯的赫克偶联具有高效的催化活性。在催化剂负载量为 5%的条件下,以中等到较高的收率(收率高达 99%)获得了预期的各种苯乙烯。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
Transition Metal Chemistry
Transition Metal Chemistry 化学-无机化学与核化学
CiteScore
3.60
自引率
0.00%
发文量
32
审稿时长
1.3 months
期刊介绍: Transition Metal Chemistry is an international journal designed to deal with all aspects of the subject embodied in the title: the preparation of transition metal-based molecular compounds of all kinds (including complexes of the Group 12 elements), their structural, physical, kinetic, catalytic and biological properties, their use in chemical synthesis as well as their application in the widest context, their role in naturally occurring systems etc. Manuscripts submitted to the journal should be of broad appeal to the readership and for this reason, papers which are confined to more specialised studies such as the measurement of solution phase equilibria or thermal decomposition studies, or papers which include extensive material on f-block elements, or papers dealing with non-molecular materials, will not normally be considered for publication. Work describing new ligands or coordination geometries must provide sufficient evidence for the confident assignment of structural formulae; this will usually take the form of one or more X-ray crystal structures.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
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
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
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 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信