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Tetrafluoropyridinyl Thiolate as a Tool for Enabling Photoredox Alkylation of 1,2,4‐Oxadiazoles Full article

Journal Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150
Output data Year: 2024, Volume: 366, Number: 16, Pages: 3505-3510 Pages count : 6 DOI: 10.1002/adsc.202400075
Authors Frumkin Alexander E. 1 , Levin Vitalij V. 1 , Dilman Alexander D. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry 119991 Moscow Leninsky prosp. 47 Russian Federation

Abstract: A method for the radical functionalization of 1,2,4-oxadiazoles using alkyl halides as precursors of radicals is described. The reaction efficiency is determined by potassium tetrafluoropyridinyl thiolate additive, which plays dual role. First, the thiolate converts alkyl halides into more reactive fluorinated aryl sulfides, which undergo photoredox activation of the C−S bond. Second, the thiolate decreases the unproductive loss of alkyl radicals by converting them back to the sulfides.
Cite: Frumkin A.E. , Levin V.V. , Dilman A.D.
Tetrafluoropyridinyl Thiolate as a Tool for Enabling Photoredox Alkylation of 1,2,4‐Oxadiazoles
Advanced Synthesis & Catalysis. 2024. V.366. N16. P.3505-3510. DOI: 10.1002/adsc.202400075 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:001191222500001
Scopus: 2-s2.0-85189001435
OpenAlex: W4392467665
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Scopus 1
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