Visible-Light-Induced Glycosylation/Annulation of 2-Isocyanobiaryls and Glycosyl NHP Esters to Access Nonclassical Heteroaryl C-Glycosides

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

Published: Jan. 13, 2025

A photoredox-promoted cascade glycosylation/cyclization reaction of 2-isocyanobiaryls and glycosyl NHP esters was established for the synthesis nonclassical heteroaryl C-glycosides. This methodology is characterized by an exceedingly simple system, high diastereoselectivity, good functional group tolerance. In contrast to traditional strategies, this innovative approach circumvents need temperature, transition metal, photocatalyst, offering environmentally friendly efficient protocol.

Language: Английский

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Visible-light-induced radical cascade cyclization of 2-isocyanobiaryls via 1,5-hydrogen atom transfer (1,5-HAT)

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

We reported the first example of visible-light-induced radical cascade cyclization 2-isocyanobiaryls via 1,5-HAT, which is characterized by broad substrate scope, excellent functional group compatibility and no requirement any metals base.

Language: Английский

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Fe-Catalyzed Radical Trifluoromethylation and Cyclization of Ortho-Vinyl Enaminones with 1-(Trifluoromethyl)-1,3-benzo-[d][1,2]iodaoxol-3(1H)-one to Construct Functionalized Quinolines

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

Published: May 19, 2025

Herein, we present a protocol for the construction of functionalized quinolines, i.e., 3-acyl-4-(2,2,2-trifluoro-ethyl)quinolines (ATFQLs) 4, from ortho-vinyl enaminones and 1-(trifluoromethyl)-1,3-benzo-[d][1,2]-iodaoxol-3(1H)-one, which was catalyzed by FeCp2 promoted FeCl3 (Lewis acid) additives in solvents (i.e., acetonitrile toluene). This strategy first utilized FeCp2-catalyzed functionalization alkenes with trifluoromethyl radicals. The intermediate formed captured ortho-iodobenzoate substrate, yielding 3, then underwent FeCl3-catalyzed elimination at higher temperature to form an α,β-unsaturated intermediate. subsequent intramolecular Michael reaction yielded final target compound 4. In summary, series ATFQLs 4 were synthesized through formation two bonds (C═C C-C).

Language: Английский

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Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2114 - 2128

Published: Aug. 26, 2024

Isocyanide is a promising synthetic reagent not only as one-carbon homologation but also nitrogen source for nitrogen-containing molecules. Because of their isoelectronic structure with carbon monoxide, isocyanides react nucleophiles, electrophiles, radicals, and transition metal reagents, are widely used in organic synthesis. On the other hand, use reactions heteroatom radicals limited. However, reaction tool construction molecules modified variety heteroatoms. In this Perspective, we review addition cyclization discuss prospects radicals.

Language: Английский

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Non-directed Oxidative Annulation of 2-Arylindazoles with Electron Deficient Olefins via Visible Light Photocatalysis

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(75), P. 10402 - 10405

Published: Jan. 1, 2024

A new visible-light-mediated non-directed oxidative annulation between 2-arylindazoles and electron-deficient olefins using commercially available piperidine-1-sulfonyl chloride as the radical precursor to afford fused 5,6-dihydroindazolo[2,3-

Language: Английский

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