2024

DOI: 10.1039/d4gc01015a

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Metal- and photocatalyst-free three-component strategy to prepare benzylalcohol-, aldehyde-substituted BCP building blocks

Fei Li,

Huijuan Liao,

Jianyang Dong

et al.

Abstract: A mild one-step, light-promoted, three-component radical-coupling reaction of [1.1.1]propellane to afford difunctionalized benzylalcohol-, aldehyde-substituted BCPs in the absence of metals, photocatalysts or external oxidants was reported.

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Cited by 7 publications

References 60 publications

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Photoinduced Multicomponent Heteroarylation of [1.1.1]Propellane with Katritzky Pyridinium Salts

Xiao,

Dong,

Wang

et al. 2024

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(Hetero)arylated bicyclo[1.1.1]pentanes (BCPs) are important for the construction of complex druglike target molecules. Herein, we developed a method for light-induced, Cs2CO3-promoted homolytic cleavage of pyridinium C–N bonds for generating alkyl radicals from amino acid-derived Katritzky salts and use of the radicals for functionalization of [1.1.1]propellane to rapidly generate (hetero)arylated BCPs. The method features excellent functional group tolerance and a broad substrate scope and can be used to functionalize structurally complex natural products.

Photoinduced Multicomponent Heteroarylation of [1.1.1]Propellane with Katritzky Pyridinium Salts

Xiao,

Dong,

Wang

et al. 2024

View full text Add to dashboard Cite

(Hetero)arylated bicyclo[1.1.1]pentanes (BCPs) are important for the construction of complex druglike target molecules. Herein, we developed a method for light-induced, Cs2CO3-promoted homolytic cleavage of pyridinium C–N bonds for generating alkyl radicals from amino acid-derived Katritzky salts and use of the radicals for functionalization of [1.1.1]propellane to rapidly generate (hetero)arylated BCPs. The method features excellent functional group tolerance and a broad substrate scope and can be used to functionalize structurally complex natural products.

Site-Specific Radical Alkylation of Aryl Cyanide: Visible-Light, Photoredox-Catalyzed, Three-Component Arylalkylation of [1.1.1]Propellane

Hou,

Guo,

Shen

et al. 2024

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We report herein a three-component radical arylalkylation of [1.1.1]propellane toward the synthesis of arylsubstituted bicyclo[1.1.1]pentane derivatives. The use of electrondeficient aryl cyanide as an aryl group source not only reduces the energy barrier of the arylation of the nucleophilic alkyl radical species, but also suppresses the electrophilic Friedel−Crafts alkylation process, enabling the present site-selective arylalkylation.

Direct Diazoarylation of [1.1.1]Propellane with Arenediazonium Salts: A Modular Assembly of Arylated Diazo Bicyclo[1.1.1]pentanes

Nan,

Cheng,

Zhang

et al. 2024

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A mild and concise diazoarylation of [1.1.1]propellane is described, which provides a modular approach to arylated diazo bicyclopentanes (BCPs). This reaction proceeds smoothly under basic conditions without requiring other additives or catalysts. The substrate scope shows that various electron-withdrawing and electron-donating groups are tolerated, and the subsequent modifications provide a novel avenue for assembling arylamino-BCP analogs.

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