56161-51-4Relevant academic research and scientific papers
Metal-free visible-light-promoted C(sp3)-H functionalization of aliphatic cyclic ethers using trace O2
Blackburn, Bryan G.,Cooke, Maria Victoria,Laulhé, Sébastien,Niu, Ben,Sachidanandan, Krishnakumar
, p. 9454 - 9459 (2021/12/09)
Presented is a light-promoted C-C bond forming reaction yielding sulfone and phosphate derivatives at room temperature in the absence of metals or photoredox catalyst. This transformation proceeds in neat conditions through an auto-oxidation mechanism which is maintained through the leaching of trace amounts of O2 as sole green oxidant. This journal is
Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step
Chan, Wei Chuen,Vinod, Jincy K.,Koide, Kazunori
, p. 3674 - 3682 (2021/02/16)
We describe a visible-light-promoted addition of a hydrogen atom and an acetal carbon toward various electron-deficient alkenes. 1,3-Dioxolane is converted to its radical species in the presence of persulfate and an iridium catalyst upon visible light irradiation, which then reacts with electron-deficient alkenes. The reaction operates via a radical chain mechanism, a less commonly observed pathway for this class of transformation. Hydrogen atom transfer from 1,3-dioxolane to α-malonyl radicals is corroborated by experimental and density functional theory studies.
Efficiency and Selectivity Aspects in the C-H Functionalization of Aliphatic Oxygen Heterocycles by Photocatalytic Hydrogen Atom Transfer
Raviola, Carlotta,Ravelli, Davide
supporting information, p. 803 - 809 (2019/04/25)
The C-H to C-C conversion in aliphatic oxygen heterocycles (dioxolanes, 1,3-dioxane, or cyclic carbonates) by photocatalytic hydrogen atom transfer and subsequent trapping of the resulting radical with phenyl vinyl sulfone was investigated. The performanc
A concise approach to anthraquinone-xanthone heterodimers
Holmbo, Stephen D.,Pronin, Sergey V.
supporting information, p. 5065 - 5068 (2018/04/24)
A synthetic approach to anthraquinone-xanthone heterodimers is described. The route to the pentacyclic core features an efficient assembly of a benzocycloheptenone via a new intramolecular oxidative arylation of an enol ether and a Hauser-Kraus annulation-aldol reaction sequence to access the characteristic bicyclo[3.2.2]nonene motif. Acremoxanthone A is synthesized in 10 steps from commercially available material to demonstrate the application of this approach.
Practical β-masked formylation and acetylation of electron-deficient olefins utilizing tetra(n-butyl)ammonium peroxydisulfate
Jung, Jae Chul,Kim, Yong Hae,Lee, Kieseung
experimental part, p. 4662 - 4664 (2011/09/30)
Various electron-deficient olefins reacted readily with 1,3-dioxolane or 2-methyl-1,3-dioxlane in the presence of TBAP to afford the corresponding 1,3-dioxolanylated or 2-methyl-1,3-dioxolanylated products in a complete regioselective manner in good to ex
Addition to electron deficient olefins of α-oxy carbon-centered radicals, generated from cyclic ethers and acetals by the reaction with alkylperoxy- λ3-iodane
Sueda, Takuya,Takeuchi, Yasunori,Suefuji, Takashi,Ochiai, Masahito
, p. 195 - 200 (2007/10/03)
Thermal decomposition of 1-tert-butylperoxy-1,2-benziodoxol-3(1H)-one in cyclic ethers and acetals at 50°C generates α-oxy carbon-centered radicals, which undergo an addition reaction with vinyl sulfones and unsaturated esters.
Oxidation of allylic alcohols, amines, and sulfides mediated by assembled triphase catalyst of phosphotungstate and non-cross-linked amphiphilic copolymer
Yamada, Yoichi M.A.,Tabata, Hidetsugu,Ichinohe, Masato,Takahashi, Hideyo,Ikegami, Shiro
, p. 4087 - 4096 (2007/10/03)
A novel catalyst PWAA, an assembled complex of phosphotungstic acid (H 3PW12O40) and a non-cross-linked copolymer of N-isopropylacrylamide with an ammonium, was developed. It is an amphiphilic, cross-linked, and supramolecular insoluble complex and showed catalytic activity on oxidation with aqueous hydrogen peroxide. PWAA, used in 2.7×10 -5-2.0×10-3molequiv., catalyzed oxidation of allylic alcohols, amines, and sulfides efficiently. The turnover number (TON) of PWAA reached up to 35,000. PWAA showed a good stability in organic/aqueous media and was reused three to five times.
Oxidation of amines and sulfides catalyzed by an assembled complex of phosphotungstate and non-cross-linked amphiphilic polymer
Yamada, Yoichi M. A.,Tabata, Hidetsugu,Takahashi, Hideyo,Ikegami, Shiro
, p. 2031 - 2034 (2007/10/03)
Oxidation of sulfides and amines was performed with an assembled catalyst of phosphotungstate and non-cross-linked amphiphilic polymer. The reactions proceeded with hydrogen peroxide under organic solvent-free conditions. This insoluble catalyst was reused five times with the turnover number up to 500.
Generation of hydroxyl radicals from 1-hydroxypyridine-2(1H)-thione and their application to organic synthesis
Boivin, J.,Crepon, E.,Zard, S. Z.
, p. 145 - 150 (2007/10/02)
Upon irradiation with visible light N-hydroxypyridine-2-thione 1 gives rise to hydroxyl radicals which can be used in radical chain reactions involving selective hydrogen abstraction as the key-step. Key Words: N-hydroxypyridine-2-thione / hydroxyl radicals
N-HYDROXY-2-PYRIDINETHIONE: A MILD AND CONVENIENT SOURCE OF HYDROXYL RADICALS
Boivin, Jean,Crepon, Elisabeth,Zard, Samir Z.
, p. 6869 - 6872 (2007/10/02)
N-Hydroxy-2-thiopyridone gives hydroxyl radicals on irradiationm with visible light and these can be incorporated in useful radical chain processes involving hydrogen abstraction.
