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Scientists from the ZIOC have shown the possibility of using organozinc compounds in radical reactions for the first time

10 january 2022 г.

Photoredox catalysis is currently gaining immense popularity due to the mild reaction conditions, tolerance to various functional groups, and environmental friendliness. Researchers from the Laboratory of Functional Organic Compounds of the Zelinsky Institute of Organic Chemistry have shown that organozinc reagents can act as precursors of alkyl radicals under conditions of photoredox catalysis. It should be noted that organozinc compounds are most often used as soft nucleophiles or radical reactions initiators. The possibility of using such substances as reagents in free radical transformations has been shown for the first time. It was found that the photocatalytic reaction of organozinc compounds with α- (trifluoromethyl) styrenes led to the formation of gem-difluorinated alkenes — valuable building blocks in organic synthesis. It is worth mentioning that the generation of Zn-organic reagents can be carried out in situ using alkyl halides and metallic zinc.

 

 

Source:

Anton A. Gladkov, Grigory N. Chernov, Vitalij V. Levin, Vladimir A. Kokorekin, Alexander D. Dilman Photoredox Activation of Organozinc Reagents: Barbier-Type Reaction of Alkyl Halides with α‑(Trifluoromethyl)styrenes Org. Lett., 2021, 23, 9645–9648. DOI: 10.1021/acs.orglett.1c03917.