An amine-promoted three-component radical selenofunctionalization reaction of alkenes with TBHP and diselenide is disclosed. The reaction conditions are mild and suitable for a wide range of substrates (29 examples), and all give the corresponding hydroxyselenenylation products in moderate to excellent yields. In addition, preliminary studies on the mechanism reveal that the current method might proceed via a radical pathway. TBHP serves as both radical initiator and the source of hydroxyl group.
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http://dx.doi.org/10.1021/acs.joc.4c02149 | DOI Listing |
J Org Chem
December 2024
College of Chemistry, Guangdong University of Petrochemical Technology, Guandu Road, Maoming, 525000, P. R. China.
An amine-promoted three-component radical selenofunctionalization reaction of alkenes with TBHP and diselenide is disclosed. The reaction conditions are mild and suitable for a wide range of substrates (29 examples), and all give the corresponding hydroxyselenenylation products in moderate to excellent yields. In addition, preliminary studies on the mechanism reveal that the current method might proceed via a radical pathway.
View Article and Find Full Text PDFJ Org Chem
October 2020
Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion; Tianjin Key Laboratory of Drug Targeting and Bioimaging, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P. R. China.
An efficient three-component domino or one-pot strategy has been developed for the synthesis of medicinally important benzothiophene and benzothiopheno[2,3-]azepinedione derivatives for the first time. Amine-promoted selective cleavage of C-S bond of thioisatin is the key step in this process. The reported methodology benefits from environmentally friendly solvent (HO), wide substrate scope, good functional group tolerance, and high reaction yields.
View Article and Find Full Text PDFJ Org Chem
September 2019
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering , Hunan Normal University, Changsha , Hunan 410081 , People's Republic of China.
A novel one-pot three-component cascade cyclization strategy for the synthesis of 2-amino-5-acylthiazoles using enaminones, cyanamide, and elemental sulfur has been developed. The reported methods have demonstrated good tolerance of various functional groups. Up to 28 2-amino-5-acylthiazole compounds bearing diverse structural differences were successfully synthesized from easily obtained starting materials with moderate to excellent yields.
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