24062-74-6Relevant academic research and scientific papers
Electrochemical oxidation-induced benzyl C–H carbonylation for the synthesis of aromatic α-diketones
Tan, Yu-Fang,Chen, Yuan,Li, Rui-Xue,Guan, Zhi,He, Yan-Hong
supporting information, (2021/12/21)
Electrochemical oxidation-induced direct carbonylation of benzyl C–H bond for the synthesis of aromatic α-diketones is described. In this process, tetrabutylammonium iodide (nBu4NI) not only acts as an electrolyte, but its iodine anion is oxidized to an iodine radical at the anode, acting as a hydrogen atom transfer agent. The iodine radical extracts the benzyl hydrogen atom and causes the carbonylation of the benzyl position, where O2 in the air is used as an oxygen source.
Palladium-catalyzed synthesis of α-aryl acetophenones from styryl ethers and aryl diazonium saltsviaregioselective Heck arylation at room temperature
Kandasamy, Jeyakumar,Lee, Yong Rok,Singh, Adesh Kumar,Venkatesh, Rapelly
supporting information, p. 7832 - 7837 (2021/09/28)
Preparation of α-aryl acetophenones from styryl ethers and aryldiazonium salts is described. The reaction is catalyzed by palladium acetate at room temperature in the absence of ligand and base. The developed method is highly attractive in terms of reaction conditions, substrate scope, functional group tolerance and yields. Synthetic applications of the present method are demonstrated by preparing α-aryl indoles and 3-aryl isocoumarin from styryl ethers.
Ruthenium(II)-Catalyzed Cross-Coupling of Benzoyl Formic Acids with Toluenes: Synthesis of 2-Phenylacetophenones
Chen, Yujie,Dai, Chenyang,Huang, Zhibin,Jiang, Yaqiqi,Shu, Sai,Yang, Shan,Zhao, Yingsheng
, p. 2955 - 2961 (2021/07/22)
Herein, we report a direct method to synthesize 2-phenylacetophenone through a ruthenium(II)-catalyzed cross-coupling reaction between acyl and benzyl radical. The various derivatives of 2-phenylacetophenone were prepared easily in moderate to good yields. These reactions provide a straightforward pathway to synthesize a variety of ketones bearing various functional groups.
Preparation of 4-Vinylbenzil and Photochemical Properties of Its Homopolymer and Copolymer with Styrene
Mosnacek, Jaroslav,Weiss, Richard G.,Lukac, Ivan
, p. 1304 - 1311 (2007/10/03)
When irradiated at >400 nm in air, pendant benzil groups of 1-phenyl-2-(4-vinylphenyl)-1,2-ethanedione/styrene (VBz/S) copolymer films are transformed almost quantitatively into benzoyl peroxide (BP) groups. Subsequent heating at 91°C converts the pendant benzoyl peroxide groups to esters and benzoic acid moieties, and there is significantly more cross-linking than main-chain cleavage. Irradiation of the VBz/S copolymer films at 366, 313, and 254 nm also results in formation of BP groups, but they are transformed in situ upon absorption of a second photon by the matrix. The ratios of the relative rate constants for BP formation and subsequent transformation upon absorption by a second photon decrease with decreasing wavelengths of radiation. Irradiation of a film composed of a nonmiscible intimate mixture of poly(1-phenyl-2-(4-vinylphenyl)-1,2-ethanedione) (PVBz) and polystyrene (PS) at >400 nm in air does not lead to discernible BP concentrations as well. Instead, the unreacted pendant benzil groups act as photosensitizers to transform the peroxy moieties almost immediately. In addition, we demonstrate that cross-linking of the VBz/S copolymer film, induced by 254 nm radiation, can be utilized to record a negative image.
Alkali metal ion controlled product selectivity during photorearrangements of 1-naphthyl phenyl acylates and dibenzyl ketones within zeolites
Warrier,Kaanumalle, Lakshmi S.,Ramamurthy
, p. 620 - 631 (2007/10/03)
Photochemical behaviors of 1-naphthyl phenyl acylates and dibenzyl ketones included in zeolites have been compared. 1-Naphthyl phenyl acylates while in solution produce eight photoproducts; within NaY it gives a single product. The selectivity is attributed to the restriction brought on the mobility of the primary radical pair by the alkali metal ions present in zeolites. Photochemistry of dibenzyl ketones within NaY reveals that the intersystem crossing in caged radical pairs could be influenced by the heavy alkali metal ions. Structures of complexes among Li+ ion and the guest 1-naphthyl phenyl acetates and dibenzyl ketone computed at the B3LYP level have been useful to understand the origin of the observed product selectivity within zeolites.
A high speed parallel synthesis of 1,2-diaryl-1-ethanones via a clean-chemistry C-C bond formation reaction
Veeramaneni, Venugopal Rao,Pal, Manojit,Yeleswarapu, Koteswar Rao
, p. 3283 - 3290 (2007/10/03)
In this report, we describe the parallel as well as conventional synthesis of 1,2-diaryl-1-ethanones via environmentally benign acylation of arenes with in situ generated arylacetyl trifluoroacetates. A wide variety of arylacetic acids I participated in trifluoroacetic anhydride/phosphoric acid mediated C-C bond formation reaction when reacted with arenes of type II to give 1,2-diaryl-1-ethanones III in good to excellent yield. Under the solvent-free conditions these chemical transformations that normally require longer reaction time can be performed within minutes in good yield.
Product Study of Some One-Electron Oxidations of Bibenzyl and 4-Ethylbibenzyl. Evidence against Carbon-Carbon Bond Cleavage of the Bibenzyl Radical Cation in Solution
Baciocchi, Enrico,Bartoli, Donatella,Rol, Cesare,Ruzziconi, Renzo,Sebastiani, Giovanni V.
, p. 3587 - 3593 (2007/10/02)
The oxidations of bibenzyl (1) and (or) 4-ethylbibenzyl (2) have been investigated under a variety of conditions, all of which should involve the intermediacy of bibenzyl radical cations: (a) reaction with ceric ammonium nitrate (CAN) in AcOH or CH3CN-H2O; (b) anodic oxidation in AcOH -CH3CN or (CH3)2CO-H2O; (c) photochemical oxidation by CAN in CH3CN; (d) photochemical autoxidation catalyzed by 9,10-dicyanoanthracene or by CAN in CH3CN.Nearly exclusive formation of side chain substituted products is observed for the chemical and electrochemical oxidations when the reactions are carried out in AcOH, CH3CN or AcOH-CH3CN, whereas extensive formation of C-C bond cleavage products occurs in the same processes when aqueous solvents are used.In the photochemical reactions, autoxidation produces both cleavage and side chain substituted products, whereas only the latter forms in the CAN-induced reaction in the absence of dioxygen.Evidence based on product analysis suggests that in these reactions no significant C-C bond breaking takes place at the state of bibenzyl radical cation.Cleavage products, where observed, nearly certainly derive from first-formed side chain substitution products
