33264-36-7Relevant 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.
Catalyst-Free and Transition-Metal-Free Approach to 1,2-Diketones via Aerobic Alkyne Oxidation
Shen, Duyi,Wang, Hongyan,Zheng, Yanan,Zhu, Xinjing,Gong, Peiwei,Wang, Bin,You, Jinmao,Zhao, Yulei,Chao, Mianran
, p. 5354 - 5361 (2021/05/05)
A catalyst-free and transition-metal-free method for the synthesis of 1,2-diketones from aerobic alkyne oxidation was reported. The oxidation of various internal alkynes, especially more challenging aryl-alkyl acetylenes, proceeded smoothly with inexpensive, easily handled, and commercially available potassium persulfate and an ambient air balloon, achieving the corresponding 1,2-diketones with up to 85% yields. Meanwhile, mechanistic studies indicated a radical process, and the two oxygen atoms in the 1,2-diketons were most likely from persulfate salts and molecular oxygen, respectively, rather than water.
Visible light-induced aerobic oxidation of diarylalkynes to α-diketones catalyzed by copper-superoxo at room temperature
Charpe, Vaibhav Pramod,Hwang, Kuo Chu,Sagadevan, Arunachalam
supporting information, p. 4426 - 4432 (2020/08/10)
We have developed the visible light induced simple copper(ii) chloride catalyzed oxidation of diarylacetylenes to α-diketones by molecular oxygen at room temperature. The in situ generated copper(ii)-superoxo complex is a light-absorbing species that oxidizes inert diarylacetylenes to α-diketones. In contrast to reported photochemical processes, the current oxidation protocol does not require any exogenous photocatalyst or radical initiator. The green chemistry metrics evaluation signifies that the E-factor for the current oxidation process is ~2.3 times better than that of reported photochemical processes. The current reaction scores 63 on the EcoScale of 0-100, indicating an adequate synthesis process. Thus, the overall oxidation process is simple, environmentally benign, and economically feasible. This journal is
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.
