Thermocontrolled Radical Nucleophilicity vs Radicophilicity in Regiodivergent C–H Functionalization

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

Published: Jan. 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.

Language: Английский

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Visible Light-Induced Sequential Nitrogen Insertion and Benzotriazolation of Quinoxaline-2(1H)-ones

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

Published: Feb. 3, 2025

Herein, we report a visible light-mediated sequential reaction involving in situ generation of benzotriazole from benzene-1,2-diamine and tert-butyl nitrite via nitrogen insertion concomitant cross-coupling with quinoxaline-2(1H)-ones C-N bond formation one pot. This protocol uses metal-free mild conditions demonstrated 36 examples ≤80% yield wide functional group tolerance.

Language: Английский

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Visible Light‐Induced Arylation/Alkylation/Phosphorylation of Isocyanides viaEDA Complex Activation

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 20, 2025

Comprehensive Summary Herein, it is reported that the aryl radicals derived from thianthrenium salts are used as coupling partner in arylation reactions of isocyanides, simultaneously initiators for formation alkyl and phosphoryl ethers diarylphosphine oxides. This cascade cyclization reaction leads to diverse arylated, alkylated phosphorylated heteroaromatic compounds. Notably, this transformation can be achieved without aid metals or photocatalysts, exhibiting a wide substrate applicability operational simplicity. Mechanistic studies suggest involvement radical processes electron donor‐acceptor (EDA) complexes transformation.

Language: Английский

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Dynamic Self-Assembled Systems of Photoinert N-Propargyl Amides Enable Red-Light Supramolecular Photocatalysis

ACS Sustainable Chemistry & Engineering, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

Language: Английский

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