Copper-catalyzed sulfonylation of N-tosylhydrazones followed by a one-pot C–N bond formation?
Organic & Biomolecular Chemistry Pub Date: 2021-05-26 DOI: 10.1039/D1OB00676B
Abstract
A new methodology to synthesize sulfonyl-N-phenylaniline derivatives via the trapping of bromo-sulfone derivatives generated from N-tosylhydrazones (NTHs) with amines is described. The reaction proved successful for a wide range of NTHs and amines and tolerated various functional groups on either coupling partner (35 examples). The mechanism was studied, and we showed that the sulfone formation does not follow a radical pathway.
Recommended Literature
- [1] Exchangeability of amino acid residues with similar physicochemical properties in coiled-coil interactions? Guiying Zhang,Maosheng Cheng,Yanni Li,Keliang Liu,Lifeng CaiChem. Commun., 2013,49, 11086-11088 10.1039/C3CC46560H
- [2] Enabling stable MnO2 matrix for aqueous zinc-ion battery cathodes? Yiding Jiao,Liqun Kang,Jasper Berry-Gair,Kit McColl,Jianwei Li,Haobo Dong,Hao Jiang,Ryan Wang,Furio Corà,Dan J. L. Brett,Ivan P. ParkinJ. Mater. Chem. A, 2020,8, 22075-22082 10.1039/D0TA08638J
- [3] Evolution of cellulose into flexible conductive green electronics: a smart strategy to fabricate sustainable electrodes for supercapacitors Tengfei Yu,Yuehan Wu,Wei Li,Bin LiRSC Adv., 2014,4, 34134-34143 10.1039/C4RA07017H
- [4] Evidence for the intrinsic nature of band-gap states electrochemically observed on atomically flat TiO2(110) surfaces? Shintaro Takata,Yoshihiro MiuraPhys. Chem. Chem. Phys., 2014,16, 24784-24789 10.1039/C4CP03280B
- [5] Enantio- & chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330 Sowmyalakshmi VenkataramanRSC Adv., 2015,5, 73807-73813 10.1039/C5RA13593A
- [6] EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis? Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” KimLab Chip, 2009,9, 1732-1739 10.1039/B821508A
- [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] Excellent energy storage performance in NaNbO3-based relaxor antiferroeic ceramics under a low electric field XuxinCheng,XiaomingChen,PengyuanFan 10.1007/s10832-022-00283-w
- [9] Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination? Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. SharadaChem. Commun., 2022,58, 1406-1409 10.1039/D1CC06097J
- [10] Enabling high-throughput single-animal gene-expression studies with molecular and micro-scale technologies Jason WanLab Chip, 2020,20, 4528-4538 10.1039/D0LC00881H
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.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)