Thermocontrolled Radical Nucleophilicity vs Radicophilicity in Regiodivergent C–H Functionalization

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 8, 2025

The temperature-dependent switching behavior of the saccharin radical is demonstrated, enabling regiodivergent C3–H and C7–H functionalization quinoxalin-2(1H)-ones. was generated through N–Br bond cleavage in N-bromosaccharin (NBSA) observed to transition between radicophile roles. At −10 °C, it utilized as a radicophile, resulting 100% C3-amination, while at +35 acted radical, leading exclusive C7-bromination. Radical nucleophilicity controlled by temperature modulation.

Язык: Английский

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Photoredox cobalt dual catalysis toward C3-functionalization of quinoxalinones with alkenes and alkynes

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A site-selective coupling involving quinoxalin-2-ones with alkenes and alkynes has been developed through synergistic visible-light photoredox cobalt catalysis.

Язык: Английский

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Photoactivation of Thianthrenium Salts: An Electron-Donor–Acceptor (EDA)-Complex Approach

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 14, 2025

Thianthrenium salts have emerged as one of the most versatile reagents, gaining significant popularity within synthetic community for their utility in construction C-C and C-X (X = N, O, S, P, halogens) bonds. The use photoredox transition metal catalysis with thianthrenium C-heteroatom bond formation is well established. However, these methods require elevated temperatures, expensive catalysts, ligands under stringent conditions effective execution. In contrast, photocatalysis- transition-metal-free approaches constructing bonds using salt derivatives become increasingly sought after. this regard, electron-donor-acceptor (EDA)-complex reactions a powerful strategy organic synthesis, eliminating need photocatalysts visible light irradiation. EDA-complex photochemistry exploits electron-acceptor properties salts, facilitating rapid generation radical intermediates via C-S cleavage. These play pivotal role enabling variety valuable formations. Perspective, we highlight advances EDA-complex-mediated involving mechanisms, substrate scope, limitations For sake brevity, article organized into five main sections: (1) Nitrogen-based donor reactions, (2) Oxygen-based (3) Sulfur-based (4) Phosphorus-based (5) π-based focus on C-C, C-S, C-B C-P

Язык: Английский

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Photo-induced aerobic cross-coupling of quinoxalin-2(1H)-ones with electron-rich thiophenes

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Herein, an efficient aerobic cross-coupling of quinoxazolines with electron-rich thiophenes was presented. It's easy and effective access to 3-thiophenyl quinoxalinones without external photo-catalyst or transition-metal catalyst.

Язык: Английский

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Electron-donor-acceptor (EDA) complex-driven regioselective vicinal and oxidative geminal functionalization of alkynes†

Chemical Communications, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

A visible-light-initiated electron-donor-acceptor (EDA) complex-driven regioselective vicinal and oxidative geminal thiosulfonylation of alkynes is presented. Organic thiosulfonates act as an acceptor, producing either sulfonyl (RSO

Язык: Английский

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Electron Donor-Acceptor Complex Enabled Photocascade Strategy for Synthesis of trans-Dihydrofuro[3,2-c]chromen-4-one Scaffolds via Radical Conjugate Addition of Pyridinium Ylide

Chemical Communications, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

A photocascade strategy is disclosed for the synthesis of trans -dihydrofurocoumarin utilising EDA complex followed by 1,4-radical conjugate addition pyridinium ylide.

Язык: Английский

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