Solvent-promoted photochemical carbonylation of benzylic C–H bonds under iron catalysis?
Organic & Biomolecular Chemistry Pub Date: 2023-06-08 DOI: 10.1039/D3OB00328K
Abstract
This paper describes the iron-catalyzed photochemical carbonylation of benzylic C–H bonds resulting in the synthesis of various aryl ketones. Using 5 W blue LED irradiation, the reactions proceed smoothly in the presence of 2 mol% of FeBr3 in MeOH at 35 °C. The catalytic system could be extended for the oxidation of silane, thioether, and phosphine into silenol, sulphoxide, and phosphoxide, respectively. A mechanistic study suggests that a hydrogen bond-stabilized iron-hydroperoxo species is the reactive intermediate. It is shown that the reaction proceeds via a four-electron-transfer pathway, and a benzylic cation seems to be the crucial reactive species. The method is applied for the synthesis of pomalyst, haloperidol, melperone, and lenperone.
Recommended Literature
- [1] Dissociative dynamics of O2 on Ag(110)? Ivor Lon?ari?Phys. Chem. Chem. Phys., 2015,17, 9436-9445 10.1039/C4CP05900J
- [2] Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation Matthew J. Gaunt,Jinquan Yu,Jonathan B. SpencerChem. Commun., 2001, 1844-1845 10.1039/B103066N
- [3] Excimer–monomer switch: a reaction-based approach for selective detection of fluoride? Qiao Song,Angela Bamesberger,Lingyun Yang,Haley Houtwed,Haishi CaoAnalyst, 2014,139, 3588-3592 10.1039/C4AN00522H
- [4] Fast synthesis of copper nanoclusters through the use of hydrogen peroxide additive and their application for the fluorescence detection of Hg2+ in water samples? Liao Xiaoqing,Li Ruiyi,Li Zaijun,Sun Xiulan,Wang Zhouping,Liu JunkangNew J. Chem., 2015,39, 5240-5248 10.1039/C5NJ00831J
- [5] Elusive 2-aminofuran Diels–Alder substrates for a straightforward synthesis of polysubstituted anilines? Ana G. Neo,Ana Bornadiego,Jesús Díaz,Stefano Marcaccini,Carlos F. MarcosOrg. Biomol. Chem., 2013,11, 6546-6555 10.1039/C3OB41411F
- [6] Evidence of rutile-to-anatase photo-induced electron transfer in mixed-phase TiO2 by solid-state NMR spectroscopy? Weili Dai,Guangjun Wu,Michael HungerChem. Commun., 2015,51, 13779-13782 10.1039/C5CC04971G
- [7] Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements Analyst, 1991,116, 1125-1130 10.1039/AN9911601125
- [8] 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
- [9] Examination of deposit in commercial diluted phosphoric acid Analyst, 1880,5, 146-147 10.1039/AN8800500146
- [10] Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita 10.1002/rcm.9494
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)