ArticleACS catalysis2022
General and Practical Route to Diverse 1-(Difluoro)alkyl-3-aryl Bicyclo[1.1.1]pentanes Enabled by an Fe-Catalyzed Multicomponent Radical Cross-Coupling Reaction.
Article in ACS catalysis, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Nickel-catalyzed radical relay enabled chemoselective fluoroalkyl-borylation of [1.1.1]propellane under kinetic control.Science advances · 2026Article
- Recent Advances in Radical Coupling Reactions Directly Involving Bicyclo[1.1.1]pentane (BCP).Topics in current chemistry (Cham) · 2025Review
- α-Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source.ChemistryOpen · 2024Review
- Fe-Catalyzed Fluoroalkyl(hetero)arylation of Vinyl Azaarenes: Rapid and Modular Synthesis of Unsymmetrical 1,1-Bis(hetero)arylalkanes.Organic letters · 2024Article
- C-F bond activation enables synthesis of aryl difluoromethyl bicyclopentanes as benzophenone-type bioisosteres.Nature communications · 2024Article
- Light-enabled scalable synthesis of bicyclo[1.1.1]pentane halides and their functionalizations.Nature synthesis · 2024Article
- Iron-Catalyzed Enantioselective Multicomponent Cross-Couplings of α-Boryl Radicals.Organic letters · 2023Article
- Expanding the chemical space of enol silyl ethers: catalytic dicarbofunctionalization enabled by iron catalysis.Chemical science · 2023Article
- Experimental and Computational Studies on Cobalt(I)-Catalyzed Regioselective Allylic Alkylation Reactions.Angewandte Chemie (International ed. in English) · 2023Article
- One-Pot Synthesis of Difluorobicyclo[1.1.1]pentanes from α-Allyldiazoacetates.Organic letters · 2023Article
- Insight into Radical Initiation, Solvent Effects, and Biphenyl Production in Iron-Bisphosphine Cross-Couplings.ACS catalysis · 2023Article
- A General and Practical Route to Functionalized Bicyclo[1.1.1]Pentane-Heteroaryls Enabled by Photocatalytic Multicomponent Heteroarylation of [1.1.1]Propellane.Angewandte Chemie (International ed. in English) · 2023Article
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6 authors.
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Abstract
Bicyclo[1.1.1]pentanes (BCPs) are of great interest to the agrochemical, materials, and pharmaceutical industries. In particular, synthetic methods to access 1,3-dicarbosubsituted BCP-aryls have recently been developed, but most protocols rely on the stepwise C-C bond formation via the initial manipulation of BCP core to make the BCP electrophile or nucleophile followed by a second step (e.g., transition-metal-mediated cross-coupling step) to form the second key BCP-aryl bond. Moreover, despite the prevalence of C-F bonds in bioactive compounds, one-pot, multicomponent cross-coupling methods to directly functionalize [1.1.1]propellane to the corresponding fluoroalkyl BCP-aryl scaffolds are lacking. In this work, we describe a conceptually different approach to access diverse (fluoro)alkyl BCP-aryls at low temperatures and fast reaction times enabled by an iron-catalyzed multicomponent radical cross-coupling reaction from readily available (fluoro)alkyl halides, [1.1.1]propellane, and Grignard reagents. Further, experimental and computational mechanistic studies provide insights into the mechanism and ligand effects on the nature of C-C bond formation. Finally, these studies are used to develop a method to rapidly access synthetic versatile (difluoro)alkyl BCP halides via bisphosphine-iron catalysis.
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