Copper-Catalyzed Diastereoselective Addition of a [1,1,1]Propellane Dimer to N-tert-Butanesulfinyl Aldimines

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

Published: March 21, 2025

[1,1,1]Propellane is typically used as a building block for the construction of bicyclo[1,1,1]pentanes and cyclobutanes. In this work, diverse chiral bi(methylenecyclobutylidene) complexes were synthesized by diastereoselective addition [1,1,1]propellane dimer to N-tert-butanesulfinyl aldimines in presence copper bipyridine. Density functional theory calculations revealed that both step regeneration catalyst contributed generation favored (Ss,S,S)-diastereomer.

Language: Английский

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Photocatalytic Difunctionalization of [1.1.1]Propellane

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

The hunt for new molecular structures to improve the efficacy of biologically active molecules is at forefront pharmaceutical chemistry. So synthetic chemists have always been busy in last few decades synthesizing and testing frameworks which would work as more efficient bioisosteres present bioactive functional groups. In this area, bicyclo[1.1.1]pentane (BCP) framework has identified a promising candidate. It being utilized bioisostere aryl, tert-butyl, alkynes, etc. Now major precursor various BCP derivatives [1.1.1]propellane functionalization drawn widespread attention organic chemist community. Over past two decades, use visible light synthesis rapidly gained popularity, it represents one most approaches aligned with principles green sustainable chemistry, several interesting papers covering photocatalytic difunctionalization also published decade. This particular field really attracted That why we decided compile review article articles related under conditions. Here review, categorized discussed three categories, namely i) without using any catalyst, ii) organocatalysts, iii) metal catalysts deeper understanding key aspects these transformations.

Language: Английский

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Site-selective Alkylation of Electron-deficient Aromatic Cycles: Visible-light Photoredox Catalyzed Radical Di-functionalization of [1.1.1]Propellane

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A visible-light photoredox-catalyzed three-component radical coupling of [1.1.1]propellane with electron-deficient aromatic cycles and Katritzky salts to access alkyl arylated bicyclo[1.1.1]pentanes was established.

Language: Английский

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Visible-light Mediated Oxidative Diels-Alder Reaction of Hydroxylamines and 1,3-Dienes

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134752 - 134752

Published: May 1, 2025

Language: Английский

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Visible-Light-Mediated Perfluoroalkylation/Thioetherification of [1.1.1]Propellane under Photocatalyst-Free Conditions

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

Published: May 29, 2025

Perfluoroalkyl-functionalized bicyclo[1.1.1]pentane (BCP) derivatives have garnered significant attention in pharmaceuticals due to their special physicochemical property; however, establishing convenient synthetic protocols for these fluorinated molecular frameworks continues present substantial methodological challenges. Herein, we report a photocatalyst and additive-free perfluoroalkylation/thioetherification of [1.1.1] propellane with disulfide ether perfluoroalkyl iodines. Such photochemistry methodology utilizing an electron donor-acceptor (EDA) complex offers green novel way obtain various BCP containing thioether groups good functional group tolerance.

Language: Английский

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Visible-light Photoredox-Catalyzed Three-Component Radical Alkyl-Acylation of [1.1.1]Propellane

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A three-component radical alkyl-acylation of [1.1.1]propellane to access a diverse array 1,3-disubstituted BCP ketone derivatives.

Language: Английский

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