Stereoselective migratory heteroaryltrifluoromethylation of allylic amines via electrosynthesis?
Green Chemistry Pub Date: 2022-07-20 DOI: 10.1039/D2GC00960A
Abstract
An electrochemically initiated heteroaryltrifluoromethylation of allylic amines was developed. The cascade reaction involved the anodic oxidation of Langlois reagent (CF3SO2Na) to generate CF3 radicals, followed by radical addition to the inactivated alkene, Smiles-type heteroaryl migration, and the reduction of nitrogen radicals. Unlike the conventional oxidative reaction mode, the SO2 molecules from the Langlois reagent and Smiles rearrangement probably served as chemical reductants in the reaction cascade, giving a redox-neutral electrosynthesis. The reaction exhibited excellent regioselectivity and stereoselectivity. It provides an efficient method for the synthesis of enantiomerically pure β-heteroaryl-γ-trifluoromethyl amines and the stereoselective late-stage modification of biologically active compounds.
Recommended Literature
- [1] Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores? Shun-Ze Zhan,Mian Li,Xiao-Ping Zhou,Dan Li,Seik Weng NgRSC Adv., 2011,1, 1457-1459 10.1039/C1RA00566A
- [2] Essential effect of the electrolyte on the mechanical and chemical degradation of LiNi0.8Co0.15Al0.05O2 cathodes upon long-term cycling?? Xiaoming Liu,Zachary D. Hood,Wangda Li,Donovan N. Leonard,Arumugam Manthiram,Miaofang ChiJ. Mater. Chem. A, 2021,9, 2111-2119 10.1039/D0TA07814J
- [3] Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China? Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing LiFood Funct., 2018,9, 4234-4245 10.1039/C8FO00787J
- [4] Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications? Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping XieNanoscale Adv., 2020,2, 3921-3932 10.1039/D0NA00381F
- [5] Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration? Ziyang Deng,Changwei Chen,Sunliang CuiRSC Adv., 2016,6, 93753-93755 10.1039/C6RA20007A
- [6] Dissociation of aryl sulfonyl phthalimide radical anions: relevance to the biological activity of arylsulfonyl amides? Abdelaziz Houmam,Emad M. HamedChem. Commun., 2012,48, 11328-11330 10.1039/C2CC36835H
- [7] 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
- [8] Evidence of pre-micellar aggregates in aqueous solution of amphiphilic PDMS–PEO block copolymer? Domenico Lombardo,Gianmarco Munaò,Pietro Calandra,Luigi Pasqua,Maria Teresa CaccamoPhys. Chem. Chem. Phys., 2019,21, 11983-11991 10.1039/C9CP02195G
- [9] Excellent mechanical performance and enhanced dielectric properties of OBC/SiO2 elastomeric nanocomposites: effect of dispersion of the SiO2 nanoparticles? Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei YangRSC Adv., 2017,7, 46297-46305 10.1039/C7RA08074C
- [10] 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
Journal Name：Green 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)