ArticleNature chemistry2024
Modular synthesis of 1,2-azaborines via ring-opening BN-isostere benzannulation.
Article in Nature chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
13 citing papers in PubMed, 31 citations in OpenAlex.
- Modular and Stereoselective Synthesis of Cyclobutane β-Amino Alcohols.Angewandte Chemie (International ed. in English) · 2026Article
- Substituent-rebound skeletal editing for precise boron-to-carbon single-atom swapping.Nature communications · 2026Article
- Article
- A Catalyst-Controlled Divergent Rearomatization of BN-Benzvalene.Journal of the American Chemical Society · 2026Article
- Positional Isomerization of 1,2-Azaborine through BN-Benzvalene.Journal of the American Chemical Society · 2026Article
- Fused 3D boron heterocyclesChemical science · 2026Article
- Core diversification using 1,2-oxaborines as a versatile molecular platform.Nature chemistry · 2026Article
- Organocatalysed three-component modular synthesis of BN isosteres and BN-2,1-azaboranaphthalenes via Wolff-type rearrangement.Nature chemistry · 2026Article
- Expedient access to bora-butenolide bioisosteres by counteranion-mediated trans-hydroboration of alkynes.Nature communications · 2025Article
- Modular enantioselective assembly of multi-substituted boron-stereogenic BODIPYs.Nature chemistry · 2025Article
- Enantioselective construction of C-B axially chiral alkenylborons by nickel-catalyzed radical relayed reductive coupling.Nature communications · 2024Article
- Transforming cyclopropanes to enamides via σ-C-C bond eliminative borylation.Nature communications · 2024Article
- Rapid and Modular Access to Multifunctionalized 1,2-Azaborines via Palladium/Norbornene Cooperative Catalysis.Journal of the American Chemical Society · 2024Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
9 authors at 4 institutions in 1 country.
Funding
Abstract
1,2-Azaborines represent a unique class of benzene isosteres that have attracted interest for developing pharmaceuticals with better potency and bioavailability. However, it remains a long-standing challenge to prepare monocyclic 1,2-azaborines, particularly multi-substituted ones, in an efficient and modular manner. Here we report a straightforward method to directly access diverse multi-substituted 1,2-azaborines from readily available cyclopropyl imines/ketones and dibromoboranes under relatively mild conditions. The reaction is scalable, shows a broad substrate scope, and tolerates a range of functional groups. The utility of this method is demonstrated in the concise syntheses of BN isosteres of a PD-1/PD-L1 inhibitor and pyrethroid insecticide, bifenthrin. Combined experimental and computational mechanistic studies suggest that the reaction pathway involves boron-mediated cyclopropane ring-opening and base-mediated elimination, followed by an unusual low-barrier 6π-electrocyclization accelerated by the BN/CC isomerism. This method is anticipated to find applications for the synthesis of BN-isostere analogues in medicinal chemistry, and the mechanistic insights gained here may guide developing other boron-mediated electrocyclizations.
Identifiers
What OpenQuestion holds
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.