Metal-free phosphine-catalyzed visible-light-induced radical cyclization of alkenes: access to cyclic <i>gem</i>-difluoroacyl scaffolds

Li, Ruowen; Li, Yicong; Liu, Yiwei; Wang, Yanzhao; Wu, Jingjing; Wu, Fanhong

doi:10.1039/d4qo00503a

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00503a

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Metal-free phosphine-catalyzed visible-light-induced radical cyclization of alkenes: access to cyclic gem-difluoroacyl scaffolds

Ruowen Li,

Yicong Li,

Yiwei Liu

et al.

Abstract: In this paper, we developed the first visible-light-induced phosphine-catalyzed radical cyclization of bromodifluoroacyl arenes with diverse alkenes, affording a variety of cyclic gem-difluoroacyl scaffolds in good to excellent yields. The...

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Cited by 3 publications

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³¹P Nuclear Magnetic Resonance Spectroscopy for Monitoring Organic Reactions and Organic Compounds

Marcos Anghinoni,

Irum,

Ur Rashid

et al. 2024

The Chemical Record

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Abstract31P NMR spectroscopy is a consolidated tool for the characterization of organophosphorus compounds and, more recently, for reaction monitoring. The evolution of organic synthesis, mainly due to the combination of elaborated building blocks with enabling technologies, generated great challenges to understand and to optimize the synthetic methodologies. In this sense, 31P NMR experiments also became a routine technique for reaction monitoring, accessing products and side products yields, chiral recognition, kinetic data, intermediates, as well as basic organic parameters, such as acid‐base and hydrogen‐bonding. This review deals with these aspects demonstrating the essential role of the 31P NMR spectroscopy. The recent publications (the last ten years) will be explored, discussing the experiments of 31P NMR and the strategies accomplished to detect and/or quantify distinct organophosphorus molecules, approaching reaction mechanism, stability, stereochemistry, and the utility as a probe.

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³¹P Nuclear Magnetic Resonance Spectroscopy for Monitoring Organic Reactions and Organic Compounds

Marcos Anghinoni,

Irum,

Ur Rashid

et al. 2024

The Chemical Record

View full text Add to dashboard Cite

show abstract

Modular Synthesis of gem-Difluorotetrahydrocarbazolone Scaffolds via Copper-Catalyzed Cascade Reaction of Bromodifluoroacetyl Indoles and Olefins

Yu,

Luo,

et al. 2024

Org. Lett.

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A novel and efficient modular synthesis of gemdifluorotetrahydrocarbazolone scaffolds via copper-catalyzed radical cascade cyclization of bromodifluoroacetyl indoles and olefins has been reported. This operationally simple protocol provides straightforward and practical access to a series of privileged gem-difluorotetrahydrocarbazolone scaffolds from readily available starting materials, with the feature of broad functional group tolerance and mild reaction conditions. Moreover, the method could be used for the late-stage functionalization of bioactive molecules, which opens up the possibility for practical applications.

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Photo-induced difluoroalkylation/cyclization of alkyne ketones: a novel strategy to access difluoroalkyl thiofavones

Song,

Luo,

Wang

et al. 2024

Chem. Commun.

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Metal-free phosphine-catalyzed visible-light-induced radical cyclization of alkenes: access to cyclic gem-difluoroacyl scaffolds

Abstract: In this paper, we developed the first visible-light-induced phosphine-catalyzed radical cyclization of bromodifluoroacyl arenes with diverse alkenes, affording a variety of cyclic gem-difluoroacyl scaffolds in good to excellent yields. The...

Cited by 3 publications

References 53 publications

³¹P Nuclear Magnetic Resonance Spectroscopy for Monitoring Organic Reactions and Organic Compounds

³¹P Nuclear Magnetic Resonance Spectroscopy for Monitoring Organic Reactions and Organic Compounds

Modular Synthesis of gem-Difluorotetrahydrocarbazolone Scaffolds via Copper-Catalyzed Cascade Reaction of Bromodifluoroacetyl Indoles and Olefins

Photo-induced difluoroalkylation/cyclization of alkyne ketones: a novel strategy to access difluoroalkyl thiofavones

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Metal-free phosphine-catalyzed visible-light-induced radical cyclization of alkenes: access to cyclic gem-difluoroacyl scaffolds

Abstract: In this paper, we developed the first visible-light-induced phosphine-catalyzed radical cyclization of bromodifluoroacyl arenes with diverse alkenes, affording a variety of cyclic gem-difluoroacyl scaffolds in good to excellent yields. The...

Cited by 3 publications

References 53 publications

31P Nuclear Magnetic Resonance Spectroscopy for Monitoring Organic Reactions and Organic Compounds

31P Nuclear Magnetic Resonance Spectroscopy for Monitoring Organic Reactions and Organic Compounds

Modular Synthesis of gem-Difluorotetrahydrocarbazolone Scaffolds via Copper-Catalyzed Cascade Reaction of Bromodifluoroacetyl Indoles and Olefins

Photo-induced difluoroalkylation/cyclization of alkyne ketones: a novel strategy to access difluoroalkyl thiofavones

Contact Info

Product

Resources

About

³¹P Nuclear Magnetic Resonance Spectroscopy for Monitoring Organic Reactions and Organic Compounds

³¹P Nuclear Magnetic Resonance Spectroscopy for Monitoring Organic Reactions and Organic Compounds