ArticleAngewandte Chemie (International ed. in English)2020
Synthesis of All-Carbon Disubstituted Bicyclo[1.1.1]pentanes by Iron-Catalyzed Kumada Cross-Coupling.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 85 citations in OpenAlex.
- Hetero[3.1.1]propellanes.Nature chemistry · 2026Article
- Trifluoromethyl Thianthrenium Salts: From Organic Synthesis to Materials.The Journal of organic chemistry · 2026Review
- Synthesis of Diverse Glycosyl Bicyclo[1.1.1]pentanes Enabled by Electrochemical Functionalization of [1.1.1]Propellane.Journal of the American Chemical Society · 2025Article
- Copper-Photoredox-Catalyzed C(spAngewandte Chemie (International ed. in English) · 2025Article
- Difunctionalization of bicyclo[1.1.0]butanes enabled by merging C-C cleavage and ruthenium-catalysed remote C-H activation.Nature synthesis · 2025Article
- Light-enabled scalable synthesis of bicyclo[1.1.1]pentane halides and their functionalizations.Nature synthesis · 2024Article
- Bicyclopentylation of Alcohols with Thianthrenium Reagents.Journal of the American Chemical Society · 2023Article
- 2-Oxabicyclo[2.1.1]hexanes as saturated bioisosteres of the ortho-substituted phenyl ring.Nature chemistry · 2023Article
- Review
- 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
- Rapid and Scalable Halosulfonylation of Strain-Release Reagents.Angewandte Chemie (International ed. in English) · 2023Article
- 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.ACS catalysis · 2022Article
- Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane.Organic letters · 2022Article
- Control of Redox-Active Ester Reactivity Enables a General Cross-Electrophile Approach to Access Arylated Strained Rings.Angewandte Chemie (International ed. in English) · 2022Article
- A Practical and Scalable Approach to Fluoro-Substituted Bicyclo[1.1.1]pentanes.Angewandte Chemie (International ed. in English) · 2022Article
- Electrophilic Activation of [1.1.1]Propellane for the Synthesis of Nitrogen-Substituted Bicyclo[1.1.1]pentanes.Angewandte Chemie (International ed. in English) · 2022Article
- Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP).The Journal of organic chemistry · 2021Article
- Oxa-spirocycles: synthesis, properties and applications.Chemical science · 2021Article
- Nickel-Catalyzed Decarboxylative Cross-Coupling of Bicyclo[1.1.1]pentyl Radicals Enabled by Electron Donor-Acceptor Complex Photoactivation.Organic letters · 2021Article
- Phenyl bioisosteres in medicinal chemistry: discovery of novel γ-secretase modulators as a potential treatment for Alzheimer's disease.RSC medicinal chemistry · 2021Article
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Authors and funding
8 authors at 3 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
1,3-Disubstituted bicyclo[1.1.1]pentanes (BCPs) are important motifs in drug design as surrogates for p-substituted arenes and alkynes. Access to all-carbon disubstituted BCPs via cross-coupling has to date been limited to use of the BCP as the organometallic component, which restricts scope due to the harsh conditions typically required for the synthesis of metallated BCPs. Here we report a general method to access 1,3-C-disubstituted BCPs from 1-iodo-bicyclo[1.1.1]pentanes (iodo-BCPs) by direct iron-catalyzed cross-coupling with aryl and heteroaryl Grignard reagents. This chemistry represents the first general use of iodo-BCPs as electrophiles in cross-coupling, and the first Kumada coupling of tertiary iodides. Benefiting from short reaction times, mild conditions, and broad scope of the coupling partners, it enables the synthesis of a wide range of 1,3-C-disubstituted BCPs including various drug analogues.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.