ArticleNature communications2024
C-F bond activation enables synthesis of aryl difluoromethyl bicyclopentanes as benzophenone-type bioisosteres.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- C(spACS electrochemistry · 2026Article
- A general photoinduced manganese-catalyzed platform for the sequential difunctionalization of [1.1.1]propellane.Science advances · 2026Article
- Radical defluoroallylation of polyfluoroalkyl compounds with alkenes via synergistic photoredox/cobalt catalysis.Nature communications · 2026Article
- Nickel-catalyzed radical relay enabled chemoselective fluoroalkyl-borylation of [1.1.1]propellane under kinetic control.Science advances · 2026Article
- Selective Synthesis of α,α-Difluoro- and α-Monofluoro Methylene Substituted Arenes by Defluoro C-C Bond Coupling.Organic letters · 2025Article
- 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
- Photo-induced decarboxylative radical cascade cyclization of unactivated alkenes: access to CF- and CFRSC advances · 2025Article
- New Opportunities to Access Fluorinated Molecules Using Organophotoredox Catalysis via C(spJACS Au · 2025Review
- Recent Advances in Radical Coupling Reactions Directly Involving Bicyclo[1.1.1]pentane (BCP).Topics in current chemistry (Cham) · 2025Review
- Defluorinative Multicomponent Cascade Reaction of Trifluoromethylarenes via Photoexcited Palladium Catalysis.JACS Au · 2024Article
- Strain-Releasing Ring-Opening Diphosphinations for the Synthesis of Diphosphine Ligands with Cyclic Backbones.JACS Au · 2024Article
- Chemo-, regio-, and stereoselective tetrafunctionalization of fluoroalkynes enables divergent synthesis of 5-7-membered azacycles.Chemical science · 2024Article
- Visible Light-Induced Radical Cascade Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CFACS omega · 2024Article
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Authors and funding
5 authors.
Funding
Abstract
Bioisosteric design has become an essential approach in the development of drug molecules. Recent advancements in synthetic methodologies have enabled the rapid adoption of this strategy into drug discovery programs. Consequently, conceptionally innovative practices would be appreciated by the medicinal chemistry community. Here we report an expeditous synthetic method for synthesizing aryl difluoromethyl bicyclopentane (ADB) as a bioisostere of the benzophenone core. This approach involves the merger of light-driven C-F bond activation and strain-release chemistry under the catalysis of a newly designed N-anionic-based organic photocatalyst. This defluorinative coupling methodology enables the direct conversion of a wide variety of commercially available trifluoromethylaromatic C-F bonds (more than 70 examples) into the corresponding difluoromethyl bicyclo[1.1.1]pentanes (BCP) arenes/difluoromethyl BCP boronates in a single step. The strategy can also be applied to [3.1.1]and [4.1.1]propellane systems, providing access to analogues with different geometries. Moreover, we have successfully used this protocol to rapidly prepare ADB-substituted analogues of the bioactive molecule Adiporon. Biological testing has shown that the ADB scaffold has the potential to enhance the pharmacological properties of benzophenone-type drug candidates.
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Registered trials
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.