Strain-release transformations of bicyclo[1.1.0]butanes and [1.1.1]propellanes

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 9, P. 100070 - 100070

Published: Feb. 28, 2024

Bicyclo[1.1.0]butanes (BCBs) and [1.1.1]propellanes (tricyclo[1.1.1.01,3]pentanes, TCPs) are structurally unique compounds with different chemical properties. Strain-release driven reactions have emerged as an atom- step-economic strategy for the organic synthesis. Using this strategy, a variety of functional ring molecules been efficiently synthesized, including various cyclobutane molecules, bicyclo[2.1.1]hexanes, bicyclo[1.1.1]pentanes, others. More specifically, these strain release-driven include aspects nucleophilic addition, radical electrophilic or transition metal catalysis. This review will discuss recent developments in strain-release transformations bicyclo[1.1.0]butanes [1.1.1]propellanes.

Language: Английский

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C(sp²)–H cyclobutylation of hydroxyarenes enabled by silver-π-acid catalysis: diastereocontrolled synthesis of 1,3-difunctionalized cyclobutanes

Chemical Science, Journal Year: 2023, Volume and Issue: 14(36), P. 9696 - 9703

Published: Jan. 1, 2023

Ring-opening of bicyclo[1.1.0]butanes (BCBs) is emerging as a powerful strategy for 1,3-difunctionalized cyclobutane synthesis. However, reported radical strain-release reactions are typically plagued with diastereoselectivity issues. Herein, an atom-economic protocol the highly chemo- and diastereoselective polar ring-opening BCBs hydroxyarenes catalyzed by π-acid catalyst AgBF4 has been developed. The use readily available starting materials, low loading, high selectivity (up to >98 : 2 d.r.), broad substrate scope, ease scale-up, versatile functionalizations products make this approach very attractive synthesis 1,1,3-trisubstituted cyclobutanes. Moreover, control experiments theoretical calculations were performed illustrate reaction mechanism selectivity.

Language: Английский

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Photochemical α-selective radical ring-opening reactions of 1,3-disubstituted acyl bicyclobutanes with alkyl halides: modular access to functionalized cyclobutenes

Chemical Science, Journal Year: 2023, Volume and Issue: 14(45), P. 13060 - 13066

Published: Jan. 1, 2023

Although ring-opening reactions of bicyclobutanes bearing electron-withdrawing groups, typically with β-selectivity, have evolved as a powerful platform for synthesis cyclobutanes, their application in the cyclobutenes remains underdeveloped. Here, novel visible light induced α-selective radical reaction 1,3-disubstituted acyl alkyl precursors functionalized is described. In particular, primary, secondary, and tertiary halides are all suitable substrates this photocatalytic transformation, providing ready access to single all-carbon quaternary center, or two contiguous centers under mild conditions.

Language: Английский

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Synthesis of Cyclobutanes and Cyclobutenes by Strain-Release-Driven Ring-Opening of Bicyclo[1.1.0]butanes

Synthesis, Journal Year: 2024, Volume and Issue: 56(24), P. 3829 - 3848

Published: Aug. 23, 2024

Abstract Cyclobutanes and cyclobutenes exhibit intriguing structures demonstrate significant biological activities diverse synthetic applications. This review aims to summarize recent progress in strain-release-driven ring-opening reactions of bicyclo[1.1.0]butanes (BCBs) synthesize these four-membered carbon rings. It outlines the strategies, regio- stereoselectivity, scope reactions, mechanistic implications catalytic process, providing a supplementary perspective existing reviews. 1 Introduction 2 Thermally Driven Nucleophilic Ring-Opening 3 Rearrangement Isomerization Reaction 4 Light-Driven 5 Transition-Metal/Lewis Acid Catalyzed 6 Conclusion Outlook

Language: Английский

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Photochemical selective difluoroalkylation reactions of bicyclobutanes: direct sustainable pathways to functionalized bioisosteres for drug discovery

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(9), P. 5512 - 5518

Published: Jan. 1, 2024

Photochemical solvent-controlled difluoromethylation and bromo-difluoromethylation reactions of bicyclobutanes are described. The method provides efficient pathways to obtain difluoroalkyl functionalized bioisosteres for drug discovery.

Language: Английский

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Ring expansion of spirocyclopropanes with stabilized sulfonium ylides: highly diastereoselective synthesis of cyclobutanes

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(34), P. 4537 - 4540

Published: Jan. 1, 2024

A novel method was devised for regioselective ring expansion of spirocyclopropanes to spirocyclobutanes with stabilized sulfonium ylides, affording 1,2- trans -disubstituted 6,8-dioxaspiro[3.5]nonane-5,9-diones without the formation any isomers.

Language: Английский

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Reductive Olefin Bicyclo[1.1.0]butane Coupling Enabled by Iron Hydride Hydrogen Atom Transfer

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 14928 - 14936

Published: Sept. 25, 2024

Language: Английский

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Palladium-catalyzed allylic amination of vinyl bicyclo[1.1.0]butanes: a strain release approach toward alkylidenecyclobutanes

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 1, 2024

Language: Английский

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Brønsted acid-catalyzed synthesis of spirocyclobutanes via heteroannulation of vinyloxyphenylbicyclobutanes with water

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(23), P. 4727 - 4731

Published: Jan. 1, 2024

We report a perchloric acid-catalyzed heteroannulation for the synthesis of spirocyclobutanes using vinyloxyphenylbicyclobutanes with water.

Language: Английский

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