Intermolecular oxidative radical fluoroalkylfluorosulfonylation of unactivated alkenes with (fluoroalkyl)trimethylsilane, silver fluoride, sulfur dioxide and N-fluorobenzenesulfonimide?
Organic Chemistry Frontiers Pub Date: 2018-12-19 DOI: 10.1039/C8QO01192C
Abstract
An intermolecular oxidative radical fluoroalkylfluorosulfonylation reaction of unactivated alkenes with convenient and commercially available (fluoroalkyl)trimethylsilane, silver fluoride, sulfur dioxide and N-fluorobenzenesulfonimide (NFSI) is described. This transformation efficiently affords various fluoroalkyl-containing alkyl sulfonyl fluorides with good functional group tolerance under mild conditions. Silver fluoroalkyl complexes as the fluoroalkyl radical source generated from (fluoroalkyl)trimethylsilane and silver fluoride may be the key intermediate.
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] Estimating and correcting interference fringes in infrared spectra in infrared hyperspectral imaging Ghazal Azarfar,Ebrahim Aboualizadeh,Nicholas M. Walter,Simona Ratti,Camilla Olivieri,Alessandra Norici,Michael Nasse,Achim Kohler,Mario GiordanoAnalyst, 2018,143, 4674-4683 10.1039/C8AN00093J
- [3] Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond? Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin LiuChem. Commun., 2018,54, 10092-10095 10.1039/C8CC05410J
- [4] Evolution and characterization of a benzylguanine-binding RNA aptamer? J. Xu,T. J. Carrocci,A. A. HoskinsChem. Commun., 2016,52, 549-552 10.1039/C5CC07605F
- [5] Evolutionary approaches in protein engineering towards biomaterial construction Brindha J.,Balamurali M. M.,Kaushik ChandaRSC Adv., 2019,9, 34720-34734 10.1039/C9RA06807D
- [6] Evolution of important glucosinolates in three common Brassica vegetables during their processing into vegetable powder and in vitro gastric digestion Nan Fu,Naphaporn Chiewchan,Xiao Dong ChenFood Funct., 2020,11, 211-220 10.1039/C9FO00811J
- [7] Enabling non-flammable Li-metal batteries via electrolyte functionalization and interface engineering? Jing Yu,Yu-Qi Lyu,Jiapeng Liu,Mohammed B. Effat,Junxiong WuJ. Mater. Chem. A, 2019,7, 17995-18002 10.1039/C9TA03784E
- [8] Establishing plasmon contribution to chemical reactions: alkoxyamines as a thermal probe? Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. MarqueChem. Sci., 2021,12, 4154-4161 10.1039/D0SC06470J
- [9] 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
- [10] Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements Analyst, 1991,116, 1125-1130 10.1039/AN9911601125
Journal Name：Organic Chemistry Frontiers
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)