Phenothiazine Sulfoxides as Active Photocatalysts for the Synthesis of γ-Lactones DOI Creative Commons
Niklas Hölter,

Nils Rendel,

Leander Spierling

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 2, 2025

N-substituted phenothiazines are prominent and highly effective organic photoredox catalysts, particularly known for their strong reducing capabilities. Despite wide utility, the closely related phenothiazine sulfoxides, which easily form upon oxidation, have been largely overlooked not explored in context of photocatalysis. Herein, we describe discovery application N-phenylphenothiazine sulfoxide as a photocatalyst reductive activation cyclic malonyl peroxides, giving access to complex γ-lactones starting from simple olefins. Detailed mechanistic studies were carried out better understand situ formation active catalyst species commercial precursor, well interconversion photocatalytic mechanism γ-lactone products. Specifically, employed broad range tools, including time-resolved spectroscopy, spectroelectrochemistry, transient UV-vis absorption voltammetry, isotopic labeling, radical trapping experiments, NMR density functional theory (DFT) calculations. The synthetic utility this protocol is demonstrated substrate scope study, highlighting facile spirocyclic γ-lactones, widely recognized biological importance.

Language: Английский

Visible-Light-Induced Redox-Neutral Difunctionalization of Alkenes and Alkynes DOI
Susmita Mondal, Sumit Ghosh, Alakananda Hajra

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(72), P. 9659 - 9691

Published: Jan. 1, 2024

The twelve principles of green chemistry illuminate the pathway in direction sustainable and eco-friendly synthesis, marking a fundamental shift synthetic organic paradigms. In this realm, harnessing power visible light for difunctionalization various skeletons without employing any external oxidant or reductant, specifically termed as redox-neutral difunctionalization, has attracted tremendous interest from chemists due to its low cost, easy availability environmentally friendly nature contrast traditional metal-catalyzed difunctionalizations. This review presents an overview recent updates on visible-light-induced reactions with literature coverage up May 2024.

Language: Английский

Citations

12
Phenothiazine Sulfoxides as Active Photocatalysts for the Synthesis of γ-Lactones DOI Creative Commons
Niklas Hölter,

Nils Rendel,

Leander Spierling

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 2, 2025

N-substituted phenothiazines are prominent and highly effective organic photoredox catalysts, particularly known for their strong reducing capabilities. Despite wide utility, the closely related phenothiazine sulfoxides, which easily form upon oxidation, have been largely overlooked not explored in context of photocatalysis. Herein, we describe discovery application N-phenylphenothiazine sulfoxide as a photocatalyst reductive activation cyclic malonyl peroxides, giving access to complex γ-lactones starting from simple olefins. Detailed mechanistic studies were carried out better understand situ formation active catalyst species commercial precursor, well interconversion photocatalytic mechanism γ-lactone products. Specifically, employed broad range tools, including time-resolved spectroscopy, spectroelectrochemistry, transient UV-vis absorption voltammetry, isotopic labeling, radical trapping experiments, NMR density functional theory (DFT) calculations. The synthetic utility this protocol is demonstrated substrate scope study, highlighting facile spirocyclic γ-lactones, widely recognized biological importance.

Language: Английский

Citations

0