A general electron donor–acceptor complex enabled cascade cyclization of alkynes to access sulfur-containing heterocycles

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(8), P. 3111 - 3116

Published: Jan. 1, 2023

A general visible light-promoted and electron–donor–acceptor complex-enabled cascade reaction of alkynes to produce functionalized sulfur-containing heterocycles under photocatalyst-, base-, oxidant- metal-free conditions was developed.

Language: Английский

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Iron‐Catalyzed Silylation and Spirocyclization of Biaryl‐Ynones: A Radical Cascade Process toward Silylated Spiro[5.5]trienones

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(9), P. 1537 - 1542

Published: March 11, 2022

Abstract Iron‐catalyzed cascade silyl radical addition/6‐ exo ‐trig cyclization/dearomatization of biaryl ynones has been developed. This approach uses silane as the precursor well silylation reagent, 1,10‐phenanthroline ligand, and tert ‐butyl hydroperoxide (TBHP) oxidant. By employing this tandem process, a series silylated spiro[5.5]trienones were prepared. magnified image

Language: Английский

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Synthesis of polychloromethylated and halogenated spiro[5,5]trienones via dearomative spirocyclization of biaryl ynones

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(33), P. 6659 - 6666

Published: Jan. 1, 2022

A selective polychloromethylation and halogenation reaction of alkynes via a radical addition/spirocyclization cascade sequence was developed, in which applying polyhaloalkanes as the precursor polyhalomethyl halogen radicals.

Language: Английский

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Rh(iii)-catalyzed sp³/sp²–C–H heteroarylations via cascade C–H activation and cyclization

Chemical Science, Journal Year: 2024, Volume and Issue: 15(17), P. 6544 - 6551

Published: Jan. 1, 2024

A Rh( iii )-catalyzed C–H indolation of 8-methylquinolines was illustrated with 2-alkynylanilines via sp 3 activation to achieve indole-tethered quinoline derivatives. Extension this methodology quinoline- N -oxide led biologically relevant oxindolyl-quinolines.

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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Photoinduced cyclization of aryl ynones with 4-alkyl-DHPs for the divergent synthesis of indenones, thioflavones and spiro[5.5]trienones

Molecular Catalysis, Journal Year: 2022, Volume and Issue: 535, P. 112819 - 112819

Published: Dec. 2, 2022

Language: Английский

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Oxidative Cyclization of Aryl Ynones with NaNO₂ for the Divergent Synthesis of NO₂‐Containing Spiro[5.5]trienones, Indenones and Thioflavones

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(21), P. 3651 - 3656

Published: Sept. 21, 2022

Abstract A K 2 S O 8 ‐promoted nitration/spirocyclization of biaryl ynones using inexpensive NaNO as nitro source has been described. This cascade reaction is triggered by nitration alkyne and followed 6‐exo‐trig spirocyclization, dearomatization, forming the NO ‐containing spiro[5.5]trienones in 63–85% yields. The present also provides a practical method for synthesis nitrated indenones thioflavones with 58–85% magnified image

Language: Английский

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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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K2S2O8-promoted radical trifluoromethylthiolation/spirocyclization for the synthesis of SCF3‑featured spiro[5,5]trienones

Tetrahedron, Journal Year: 2022, Volume and Issue: 106-107, P. 132649 - 132649

Published: Jan. 1, 2022

Language: Английский

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