Photoredox/Cobalt-Catalyzed Cascade Oxidative Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles under Oxidant-Free Conditions

被引:11
作者
Li, Jun-Li [1 ]
Li, Hao-Yuan [1 ]
Zhang, Shan-Shan [1 ]
Shen, Shigang [1 ]
Yang, Xiu-Long [1 ]
Niu, Xiaoying [1 ,2 ]
机构
[1] Hebei Univ, Key Lab Med Chem & Mol Diag, Key Lab Analyt Sci & Technol Hebei Prov, Coll Chem & Mat Sci,,Minist Educ, Baoding 071002, Hebei, Peoples R China
[2] Hebei Univ, Affiliated Coll Chem & Mat Sci, Postdoctoral Res Stn Chem, Baoding 071002, Peoples R China
关键词
ONE-POT SYNTHESIS; CYCLIZATION; RADICALS; ALKYL; FUNCTIONALIZATION; OXADIAZOLES; ALKENES; ACYLHYDRAZONES; HYDROGENATION; DERIVATIVES;
D O I
10.1021/acs.joc.3c01078
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient oxidant-free, photoredox-mediated cascade cyclization strategy for the synthesis of 1,3,4-oxadiazoles by using an organo acridinium photocatalyst and a cobaloxime catalyst has been developed. Various acylhydrazones have been transformed into the corresponding 1,3,4-oxadiazole products in up to 96% yield, and H2 is the only byproduct. Mechanistic experiments and density functional theory (DFT) calculation studies indicate carbon-centered radicals rather than oxygen-centered radicals as pi-radicals produced by the oxidation of photoexcited Mes-Acr(+*) along with deprotonation, which is responsible for this transformation. The practical utility of this method is highlighted by the one-pot gram-scale synthesis starting directly from commercially available aldehydes and acylhydrazides.
引用
收藏
页码:14874 / 14886
页数:13
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