Visible-light photocatalytic preparation of alkenyl thioethers from 1,2,3-thiadiazoles and Hantzsch esters: synthetic and mechanistic investigations was written by Liang, Zhanqun;Lv, Kang;Zhou, Shaofang;Zhu, Changlei;Bao, Xiaoguang. And the article was included in Organic Chemistry Frontiers in 2021.Electric Literature of C9H10O3S This article mentions the following:
A protocol to synthesize trisubstituted alkenyl thioethers I (R1 = Ph, 3-ClC6H4, 2-naphthyl, 2-thienyl, etc.; R2 = i-Pr, cyclohexyl, PhCH2, PhCMe2, etc.) through a direct S-alkylation of 1,2,3-thiadiazoles II with C-radical precursors, 4-alkyl-1,4-dihydropyridines III (R3 = EtO2C, t-BuO2C, CN), driven by visible-light photocatalysis is disclosed. A broad range of primary, secondary and tertiary C-radical precursors is suitable for this reaction and the desired products can be obtained in good to excellent yields under mild conditions. Remarkably, high stereoselectivity with Z-alkenyl thioethers was achieved in the presence of a Cu(OAc)2 catalyst. Synergistic exptl. and computational studies were carried out to shed light on the mechanisms of this reaction, in which the quenching pathway of an excited photocatalyst (*RuII) could be altered in the presence of the Cu(OAc)2 catalyst. A reductive quenching pathway (RuII/*RuII/RuI/RuII) was proposed in the absence of the Cu(OAc)2 catalyst while an oxidative quenching pathway (RuII/*RuII/RuIII/RuII) was suggested with the assistance of the Cu(OAc)2 catalyst. In addition, the origin of the Z-selectivity of the product was discussed. In the experiment, the researchers used many compounds, for example, Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8Electric Literature of C9H10O3S).
Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Electric Literature of C9H10O3S
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics