Intramolecular C–H insertion vs. Friedel–Crafts coupling induced by silyl cation-promoted C–F activation?
Organic Chemistry Frontiers Pub Date: 2015-07-03 DOI: 10.1039/C5QO00170F
Abstract
Silyl cation-promoted aryl C–F activation can lead to formal C–H activation and the formation of new C(ar)–C(alkyl) bonds. Deuterium-labeling experiments suggest an insertion of a phenyl cation into the C–H bond. From competition experiments, a relation between reaction rate and C–H bond strength could be established. Mechanistic parallels are drawn to the Mascarelli reaction.
Recommended Literature
- [1] An integrated chip for immunofluorescence and its application to analyze lysosomal storage disorders Jie Shen,Ying Zhou,Tu Lu,Junya Peng,Zhixiang Lin,Yuhong Pang,Li YuLab Chip, 2012,12, 317-324 10.1039/C1LC20845D
- [2] An approach towards the synthesis of novel fused nitrogen tricyclic heterocyclic scaffolds via GBB reaction? Sandip Gangadhar Balwe,Yeon Tae JeongOrg. Biomol. Chem., 2018,16, 1287-1296 10.1039/C7OB02933K
- [3] Alternative donor substrates for inverting and retaining glycosyltransferases? Luke L. Lairson,Warren W. WakarchukChem. Commun., 2007, 365-367 10.1039/B614636H
- [4] 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
- [5] Alt-proteins: A promising future 10.1002/fsat.3701_10.x
- [6] An interplay between electronic and structural effects on the photoluminescence decay mechanisms in LaPO4·nH2O:Tb3+ and LaPO4:Tb3+ single-crystal nanorods? M. T. Colomer,S. Díaz-Moreno,A. Tamayo,A. L. OrtizJ. Mater. Chem. C, 2018,6, 12643-12651 10.1039/C8TC03187H
- [7] An integrated droplet-digital microfluidic system for on-demand droplet creation, mixing, incubation, and sorting? Lab Chip, 2019,19, 524-535 10.1039/C8LC01170B
- [8] Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. BudaPhys. Chem. Chem. Phys., 2011,13, 10270-10279 10.1039/C1CP20213H
- [9] An aptasensor for the detection of ampicillin in milk using a personal glucose meter Xixi Li,Nanwei Zhu,Ruohan Li,Qinpu ZhangAnal. Methods, 2020,12, 3376-3381 10.1039/D0AY00256A
- [10] An amorphous Cu–In–S nanoparticle-based precursor ink with improved atom economy for CuInSe2 solar cells with 10.85% efficiency? Green Chem., 2017,19, 1268-1277 10.1039/C6GC03280J
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)