Visible-light-induced tandem ring opening/1,6-conjugate addition of cyclobutanols with p-quinone methides under metal- and additive-free conditions

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(3), P. 1375 - 1380

Published: Jan. 1, 2024

A visible-light-mediated tandem ring opening/1,6-conjugate addition of cyclobutanols with p -quinone methides was developed. This protocol allowed the formation δ,δ-diaryl ketones in presence a readily available organic photocatalyst.

Language: Английский

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Visible-light-driven selective difluoroalkylation of α-CF₃ alkenes to access CF₂-containing gem-difluoroalkenes and trifluoromethylalkanes

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(2), P. 458 - 465

Published: Nov. 23, 2023

A visible-light-mediated selective difluoroalkylation of α-trifluoromethyl alkenes with difluoroalkylating reagents was developed. This protocol allowed the formation gem -difluoroalkene difluoroacetates and trifluoromethylated difluoroacetamides.

Language: Английский

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Photoredox-Catalyzed Trifluoromethylamination of Alkenes with Concomitant Introduction of a Quinoxalin-2(1H)-one Moiety

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

Published: May 2, 2025

A photoredox-catalyzed strategy for the difunctionalization of alkenes with quinoxalin-2(1H)-ones and N-CF3 hydroxylamine reagents was developed. This reaction carried out under photoirradiation conditions, affording corresponding three-component coupling products in moderate to high yields excellent regioselectivity. It provides a new protocol access valuable quinoxalin-2(1H)-one derivatives containing group.

Language: Английский

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Visible-Light-Driven C,N-Selective Heteroarylation of N-Fluoroalkyl Hydroxylamine Reagents with Quinoxalin-2(1H)-ones

Organic Letters, Journal Year: 2023, Volume and Issue: 25(48), P. 8693 - 8699

Published: Nov. 22, 2023

Herein, we disclose a direct and powerful strategy for the synthesis of highly valuable α-trifluoromethylamine N-trifluoroethylamine derivatives from visible-light-promoted C,N-selective heteroarylation N-trifluoroethyl hydroxylamine reagents with quinoxalin-2(1H)-ones under ambient conditions. The chemoselectivity process (trifluoroalkylation or N-trifluoroethylamination) can easily be dictated modulated by selection substrates. key to success is protecting group on N atom reagents, which control 1,2-H shift in situ-generated radical. Remarkable features this method include mild conditions, easy operation, high selectivity, excellent functional tolerability. More importantly, trifluoroalkylated products readily derivatized into other interesting imidazo-fused heterocycles that would great potential exploitation pharmaceutically relevant molecules.

Language: Английский

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Visible Light‐Induced EDA‐Complex Triggered Annulative Difunctionalization via Olefin‐Olefin Coupling and Radical Truce‐Smiles Rearrangement

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(1), P. 148 - 153

Published: Dec. 9, 2023

Abstract An EDA complex comprising N ‐allyl bromodifluoroacetamides and tertiary alkyl amine was exploited to facilitate annulative difunctionalization reaction under visible‐light irradiation. This external photocatalyst‐free methodology garners olefin‐olefin coupling featuring a radical Truce‐Smiles rearrangement produced long‐chain functionalized gem ‐difluoropyrrolidones from N‐ substituted methacryloyl sulfonamides, while simple ‐aryl methacrylamides furnished pyrrolidinone‐oxindole hybrid lactams in high yields. Mechanistic investigations substantiate combined mechanism, involving charge‐transfer complex‐based cascade, alongside an α‐aminoalkyl radical‐triggered XAT process, exhibiting quantum yield value of 1.48.

Language: Английский

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NHC Catalyzed Radical Tandem Cyclization: An Efficient Synthesis of α,α-Difluoro-γ-lactam Derivatives

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(34), P. 6988 - 6998

Published: Jan. 1, 2024

Herein, an N-heterocyclic carbene (NHC) catalyzed radical tandem cyclization reaction of

Language: Английский

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Radical Cyclization-Initiated Difunctionalization Reactions of Alkenes and Alkynes

Molecules, Journal Year: 2024, Volume and Issue: 29(11), P. 2559 - 2559

Published: May 29, 2024

Radical reactions are powerful in the synthesis of diverse molecular scaffolds bearing functional groups. In previous review articles, we have presented 1,2-difunctionalizations, remote 1,3-, 1,4-, 1,5-, 1,6- and 1,7-difunctionalizations, addition followed by cyclization reactions. Presented this paper is radical second functionalization reaction. The could be realized atom transfer reactions, or transition metal-assisted coupling with neutral molecules, cationic anionic species.

Language: Английский

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Selectfluor Mediated Direct C–H Fluorination of 3-Heteroaryl-Oxindoles

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 740 - 747

Published: Dec. 15, 2023

An efficient transition-metal-free fluorination synthesis of

Language: Английский

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Photo‐catalyzed Stereospecific Synthesis of Trisubstituted Alkenes Incorporating 3,3‐Difluoro‐γ‐Lactams from Morita‐Baylis‐Hillman Acetates and N‐Allylbromodifluoroacetamides

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 1, 2024

Abstract A photocatalytic methodology has been devised for the stereoselective construction of trisubstituted alkenes incorporating 3,3‐difluoro‐γ‐lactams in 17–93% yields via a radical cascade process utilizing MBH acetates and N ‐allylbromodifluoroacetamides as starting materials. The reaction mechanism involves single‐electron transfer, 5 ‐ exo trig cyclization, addition, elimination fashion.

Language: Английский

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