Sonogashira reactions of alkyl halides catalyzed by NHC [CNN] pincer nickel(ii) complexes?
New Journal of Chemistry Pub Date: 2018-05-28 DOI: 10.1039/C8NJ02138D
Abstract
C(carbene)N(amido)N(amine)-pincer nickel(II) complexes [iPrCNN-Ni-Br] (6), [nBuCNN-Ni-Br] (7) and [BnCNN-Ni-Cl] (8) were synthesized. The catalytic performance of complexes 6–8 for Sonogashira cross-coupling reactions was explored. In a combination of 5 mol% catalyst loading of 6 and CuI/Cs2CO3/NaI/DMSO at different temperatures for the coupling reactions between alkyl iodides, bromides, chlorides and terminal alkynes, the corresponding coupling products were obtained in moderate to excellent yields. The mechanism of these catalytic reactions was discussed and partially supported by experiments. The phenylethynyl CNN pincer nickel complex 9 as a catalytically active complex was isolated and structurally characterized using X-ray diffraction.
![Graphical abstract: Sonogashira reactions of alkyl halides catalyzed by NHC [CNN] pincer nickel(ii) complexes](http://scimg.chem960.com/usr/1/C8NJ02138D.jpg)
Recommended Literature
- [1] Acetylcholinesterase amperometric detection system based on a cobalt(II) tetraphenylporphyrin-modified electrode Analyst, 1996,121, 1123-1126 10.1039/AN9962101123
- [2] Alumina grafted SBA-15 sustainable bifunctional catalysts for direct cross-coupling of benzylic alcohols to diarylmethanes? Chandran Rajendran,Govindaswamy Satishkumar,Charlotte Lang,Eric M. GaigneauxCatal. Sci. Technol., 2020,10, 2583-2592 10.1039/D0CY00471E
- [3] Achieving crystal-induced room temperature phosphorescence and reversible photochromic properties by strong intermolecular interactions? Fuming Xiao,Mengzhu Wang,Yunxiang Lei,Wenbo Dai,Yunbing Zhou,Miaochang Liu,Wenxia Gao,Xiaobo Huang,Huayue WuJ. Mater. Chem. C, 2020,8, 17410-17416 10.1039/D0TC03980B
- [4] Aggregation-induced emission of luminol: a novel strategy for fluorescence ratiometric detection of ALP and As(v) with high sensitivity and selectivity? Yuan-Jun Tong,Lu-Dan Yu,Lu-Lu Wu,Shu-Ping Cao,Ru-Ping Liang,Li Zhang,Xing-Hua Xia,Jian-Ding QiuChem. Commun., 2018,54, 7487-7490 10.1039/C8CC03725F
- [5] Alternative mixtures to R-600a. Theoretical assessment and experimental energy evaluation of binary mixtures in a commercial cooler: Mélanges alternatifs au R-600a. évaluation théorique et évaluation énergétique expérimentale de mélanges binaires dans un refroidisseur commercial. DanielCalleja-Anta,DanielSánchez,LauraNebot-Andres,RamónCabello,RodrigoLlopis 10.1016/j.ijrefrig.2023.05.009
- [6] An approach to asymmetric synthesis of β-aryl alanines by Pd(0)-catalyzed cross-coupling and cyanate-to-isocyanate rearrangement? Piotr Szcze?niak,Sebastian SteckoRSC Adv., 2015,5, 30882-30888 10.1039/C5RA02818C
- [7] Achieving Efficient Uranium Extraction by In-situ Ultrasonic Texturization of Commercial Fe Powder BomingZhu,HongweiWu,JieKang,XiaofangYu,TaoChen,RuCheng,GuolinYang,WencaiBai,WenkunZhu,RongHe 10.1039/d3en00269a
- [8] An amphipathic trans-acting phosphorothioate RNA element delivers an uncharged phosphorodiamidate morpholino sequence in mdx mouse myotubes? H. V. Jain,D. Verthelyi,S. L. BeaucageRSC Adv., 2017,7, 42519-42528 10.1039/C7RA04247G
- [9] Aggregated-fluorescent detection of PFAS with a simple chip Cheng Fang,Jinjian Wu,Zahra Sobhani,Md. Al Amin,Youhong TangAnal. Methods, 2019,11, 163-170 10.1039/C8AY02382D
- [10] An antioxidative galactomannan extracted from Chinese Sesbania cannabina enhances immune activation of macrophage cells? Chongyang Zhu,Xiaojia Bian,Xin Jia,Ning Tang,Yongqiang ChengFood Funct., 2020,11, 10635-10644 10.1039/D0FO02131H
Journal Name：New Journal of Chemistry
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)