Liang, Zhanqun; Lv, Kang; Zhou, Shaofang; Zhu, Changlei; Bao, Xiaoguang published an article in 2021. The article was titled 《Visible-light photocatalytic preparation of alkenyl thioethers from 1,2,3-thiadiazoles and Hantzsch esters: synthetic and mechanistic investigations》, and you may find the article in Organic Chemistry Frontiers.Electric Literature of C9H10O2 The information in the text is summarized as follows:
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 experimental materials used by the author, we found 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Electric Literature of C9H10O2)
2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) is a non-natural aldehyde. It undergoes enantioselective Mukaiyama aldol reaction with silylketene acetal nucleophiles in the presence of C2-symmetric bis(oxazolinyl)pyridine Cu(II) complex (catalyst).Electric Literature of C9H10O2
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem