Organocatalytic radical aminoacylation of alkenes for β-aminoketone synthesis

Jialingbieke, Ayisenbati; Hu, Xinying; Liu, Zuquan; Lin, Xiyun; Yin, Yiwen; Li, Jibin; Huang, Yatian; Du, Ding

doi:10.1007/s11426-024-2230-4

Sci. China Chem.

2024

DOI: 10.1007/s11426-024-2230-4

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Organocatalytic radical aminoacylation of alkenes for β-aminoketone synthesis

Ayisenbati Jialingbieke,

Xinying Hu,

Zuquan Liu

et al.

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Dual N-Heterocyclic Carbene/Photoredox-Catalyzed Coupling of Acyl Fluorides and Alkyl Silanes

Jakob,

Steiner,

Göbel

et al. 2024

ACS Catal.

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The combination of N-heterocyclic carbene (NHC) organocatalysis with photochemical activation is becoming increasingly established as an approach for conducting radical organic reactions under mild and practical conditions. As comparatively easy to prepare and handle organic compounds, alkyl silanes are attractive substrates for radical chemistry as desilylative mesolysis of the corresponding radical cations is known to be rapid. Here, we report the successful application of benzyl silane derivatives as source of alkyl radicals in dual NHC/ photoredox-catalyzed radical−radical coupling reactions with acyl fluorides. Relatively electron-rich benzyl silanes reacted smoothly to afford the corresponding ketones in generally good yields, while optimization of the NHC and photocatalyst allowed for a wider scope including primary benzyl substrates. Furthermore, initial experiments revealed that organosilanes bearing N-, O-and S-heteroatoms can also serve as alkyl radical sources under these conditions.

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Dual N-Heterocyclic Carbene/Photoredox-Catalyzed Coupling of Acyl Fluorides and Alkyl Silanes

Jakob,

Steiner,

Göbel

et al. 2024

ACS Catal.

View full text Add to dashboard Cite

show abstract

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Organocatalytic radical aminoacylation of alkenes for β-aminoketone synthesis

Cited by 1 publication

References 57 publications

Dual N-Heterocyclic Carbene/Photoredox-Catalyzed Coupling of Acyl Fluorides and Alkyl Silanes

Dual N-Heterocyclic Carbene/Photoredox-Catalyzed Coupling of Acyl Fluorides and Alkyl Silanes

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