Nitro-Spirocyclization of Biaryl Ynones with tert-Butyl Nitrite: Access to NO₂-Substituted Spiro[5,5]trienones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4854 - 4862

Published: March 22, 2023

A metal/peroxide-free involved simple cascade 6-exo-trig spirocyclization of tert-butyl nitrite with biaryl ynones has been finished, which resulted in various NO2-modified spiro[5,5]trienones good regioselectivity/yields. variety scaled-up experiments, reduction/epoxidation operations, and mechanistic studies were performed to verify the merits process this radical system. Finally, structure spirocycles was confirmed by single-crystal X-ray diffraction.

Language: Английский

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Divergent Construction of Thiochromanes and N-Arylbutanamides via Arylthiodifluoromethyl Radical-Triggered Cascade of Alkenes

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 13279 - 13290

Published: Aug. 31, 2023

A strategy utilizing silver-catalyzed oxidative decarboxylation radical cascade cyclization of arylthiodifluoroacetic acids with alkenes for the simple and efficient preparation difluoromethylated thiochromanes 2,2-disubstituted-N-arylbutanamides derivatives has been developed. This approach includes good functional group tolerance, easily accessible starting materials, operational simplicity.

Language: Английский

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Radical Three-Component Nitro Spiro-Cyclization of Unsaturated Sulfonamides/Amides to Access NO₂-Featured 4-Azaspiro[4.5]decanes

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3069 - 3074

Published: April 1, 2024

Free radical three-component nitration/spirocyclization of unsaturated sulfonamides/amides with tert-butyl nitrite was developed for the construction diverse NO2-revised 4-azaspiro[4.5]decanes. This tandem system featured metal-free participation, simple operation, good selectivity/yields, and a green/low-cost O source. Meanwhile, one nitro-containing complex molecule scaled-up operation were performed well to test synthetic potential cascade reaction. Isotopic labeling, inhibition experiments, DFT analysis carried out gain insight into reaction process.

Language: Английский

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EDA Complex-Enabled Annulation to Access CF₂-Containing Tetralones and Quinazolinones Using Persulfates as Electron Donors

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10614 - 10623

Published: July 25, 2024

A photocatalyst-free and EDA complex-enabled radical cascade cyclization reaction of inactive alkenes with bromodifluoroacetamides was reported for the divergent synthesis fluorine-containing tetralones quinazolinones. In this transformation, persulfates as electron donors difluoro bromamide acceptors generate complex. This is a promising photochemical method advantages such mild conditions, simple operation, being metal-free, excellent functional group tolerance.

Language: Английский

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Study on the Application of Photoelectric Technology in the Synthesis of Selenium-Containing Heterocycles

Chinese Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 41(12), P. 4588 - 4588

Published: Jan. 1, 2021

Selenium-containing heterocycles are a kind of important organic molecules, which widely used in medicine, agrochemicals, materials and other fields.Therefore, the introduction selenium atom into molecules is great significance synthetic chemistry.Visible light electrochemical technology one green sustainable synthesis methods, has opened up broad application prospects fields bifunctionalization cyclization unsaturated bonds direct functionalization C-H bonds.In recent years, development novel reaction using photoelectric to drive selenization attracted much attention.Therefore, this paper describes electrochemical-driven visible-light-induced reactions selenium-containing heterocycles, discusses applicable scope mechanism some reactions.

Language: Английский

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