Oxidative C(sp3)–H amidation of tertiary arylamines with nitriles?
Organic Chemistry Frontiers Pub Date: 2018-09-03 DOI: 10.1039/C8QO00794B
Abstract
The first amidation of tertiary arylamines with nitriles via a cascade dehydrogenation/heterocoupling/addition reaction between α-C–H bonds of tertiary amines and nitrogen atoms of nitriles has been developed. The use of copper(I) iodide as a Lewis acid catalyst, N-hydroxyphthalimide as a free radical initiator, and 2,2,6,6-tetramethylpiperidine 1-oxyl as not only an oxidant but also a nucleophile enabled the conversion of tertiary aromatic amines with nitriles into secondary amides.
Recommended Literature
- [1] Dissociative electron attachment to HGaF4 Lewis–Br?nsted superacid Marcin Czapla,Jack SimonsPhys. Chem. Chem. Phys., 2018,20, 21739-21745 10.1039/C8CP04007A
- [2] Fe3O4 nanosphere@microporous organic networks: enhanced anode performances in lithium ion batteries through carbonization? Byungho Lim,Jaewon Jin,Jin Yoo,Seung Yong Han,Kyeongyeol Kim,Sungah Kang,Nojin Park,Sang Moon Lee,Hae Jin Kim,Seung Uk SonChem. Commun., 2014,50, 7723-7726 10.1039/C4CC02068E
- [3] Enabling chloride salts for thermal energy storage: implications of salt purity? J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. MayesRSC Adv., 2019,9, 25602-25608 10.1039/C9RA03133B
- [4] Emerging investigator series: bacteriophages as nano engineering tools for quality monitoring and pathogen detection in water and wastewater Fereshteh BayatEnviron. Sci.: Nano, 2021,8, 367-389 10.1039/D0EN00962H
- [5] Distinct roles of SNARE-mimicking lipopeptides during initial steps of membrane fusion? Alena Koukalová,?árka Pokorná,Aimee L. Boyle,Nestor Lopez Mora,Alexander Kros,Martin Hof,Radek ?achlNanoscale, 2018,10, 19064-19073 10.1039/C8NR05730C
- [6] Empowering microfluidics by micro-3D printing and solution-based mineral coating? Hongxia Li,Aikifa Raza,Qiaoyu Ge,Jin-You Lu,TieJun ZhangSoft Matter, 2020,16, 6841-6849 10.1039/D0SM00958J
- [7] Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR? Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing XiaNanoscale, 2020,12, 20456-20466 10.1039/D0NR04995F
- [8] Fe3O4/Au/Fe3O4 nanoflowers exhibiting tunable saturation magnetization and enhanced bioconjugation Feng Shi,Kunping Yan,Mingli Peng,Xiao Cheng,Yanling Luo,Xuemei Chen,V. A. L. Roy,Zuankai WangNanoscale, 2012,4, 747-751 10.1039/C2NR11489E
- [9] Excellent energy storage performance in NaNbO3-based relaxor antiferroeic ceramics under a low electric field XuxinCheng,XiaomingChen,PengyuanFan 10.1007/s10832-022-00283-w
- [10] Evolutionary approaches in protein engineering towards biomaterial construction Brindha J.,Balamurali M. M.,Kaushik ChandaRSC Adv., 2019,9, 34720-34734 10.1039/C9RA06807D
Journal Name：Organic Chemistry Frontiers
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)