Visible Light-Promoted Aromatization-Driven Deconstructive Fluorination of Spiro Carbocycles

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7442 - 7446

Published: Aug. 26, 2024

A visible light-promoted aromatization-driven deconstructive fluorination of spiro carbocycles is presented. series dihydroquinazolinones reacted efficiently with NFSI under light irradiation to afford the 2-(4-fluoroalkyl)quinazolin-4(3H)-ones in good yields excellent functional group tolerance. radical pathway involving C–C bond cleavage and F atom transfer proposed for reaction. In addition, ring-opening chlorination NCS was also applicable.

Language: Английский

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Hydride Transfer-Enabled Dearomative Spirocyclization of Isoxazoles with O-Alkyl ortho-Oxybenzaldehydes

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 17, 2025

The TfOH-catalyzed dearomative [5 + 1] annulations were developed for the construction of chromane-fused spiroisoxazolines from readily available 5-amino-isoxazoles and O-alkyl ortho-oxybenzaldehydes. "two-birds-with-one-stone" strategy featuring dearomatization α-C(sp3)–H bond functionalization oxygen was disclosed via a cascade condensation/[1,5]-hydride transfer/dearomative spirocyclization process. In addition, unprecedented direct isoxazoles achieved, which introduced new family member chemistry.

Language: Английский

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Construction of C–S and C–Se Bonds via Photocatalytic Aromatization-Driven Deconstructive Diversification of Spiro-Dihydroquinazolinones Derived from Unstrained Ketones

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 13, 2025

A novel and robust deconstructive functionalization reaction of spiro-dihydroquinazolinones with sulfenylating reagents in the presence base has been realized under visible light irradiation. This enabled direct ring-opening unstrained cyclic ring systems, producing skeletally diverse functionalized quinazolinones moderate to good yields. range variety including diaryl disulfide, thiosulfonate, dithiosulfonate 1-[(trifluoromethyl)thio]-2,5-pyrrolidinedione were compatible for this transformation. In addition, diselenide selenosulfonate could also couple form C-Se Bonds. Mechanistic studies revealed that proceeds via a radical-radical coupling pathway.

Language: Английский

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Aerobic alcoholization via aromatization driven C–C bond cleavage of unstrained ketones

Green Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel aerobic aldolization approach that employs aromatization-driven C–C bond cleavage for the deacetylation of unstrained ketones was reported. Various primary and secondary alcohols were generated under oxygen atmosphere without any catalysts.

Language: Английский

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Regioselective C-C bond cleavage/aminocarbonylation cascade under copper catalysis

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 28, 2024

Language: Английский

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Photoinduced Aromatization-Driven Deconstructive Fluorosulfonylation of Spiro Dihydroquinazolinones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 30, 2024

A catalyst-free photoinduced deconstructive fluorosulfonylation cascade of spiro dihydroquinazolinones with DABSO and NFSI is reported. This protocol features mild reaction conditions, good yields excellent functional group tolerance, providing a practical approach to the quinazolin-4(1H)-one-functionalized aliphatic sulfonyl fluorides. In addition, ease gram-scale synthesis versatility SuFEx exchange highlight application potential this protocol.

Language: Английский

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