ArticleScience (New York, N.Y.)2018
Heterobiaryl synthesis by contractive C-C coupling via P(V) intermediates.
Article in Science (New York, N.Y.), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 59 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
59 citing papers in PubMed, 221 citations in OpenAlex.
- Speciation-Controlled C-F Bond Functionalization Enabled by Zwitterionic Pnictinidenes.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Substituent-rebound skeletal editing for precise boron-to-carbon single-atom swapping.Nature communications · 2026Article
- Deoxygenative Single-Carbon Atom Transfer: Accessing Strained Carbocycles From Alkenes and Aldehydes With Designer Dual-Functional Reagent.Angewandte Chemie (International ed. in English) · 2026Article
- Cyclic sulfone ring remodeling enables molecular shape diversity-oriented synthesis of privileged biaryl and oligoaryl motifs.Nature communications · 2026Article
- Phosphonium Ions as Activating Groups for the Selective Alkylation of Pyridines and Polyazines.Journal of the American Chemical Society · 2026Article
- Room-temperature electrochemical hydroxyalkylation of pyridines.Nature communications · 2026Article
- Article
- Activation of Cyanate Anions by Phosphine Radical Cations Enables Formal Hydrocarbamoylation of Alkenes.Angewandte Chemie (International ed. in English) · 2026Article
- Frame-Shifted Synthesis of Oligoheterocycles as a Platform for Molecular Design.Angewandte Chemie (International ed. in English) · 2026Article
- Ring Strain-Promoted Activation of Pyridines by a Saturated BSiAngewandte Chemie (International ed. in English) · 2026Article
- Ligand-Controlled Chemodivergent Bismuth Catalysis.Journal of the American Chemical Society · 2025Article
- Bis-Oxadiazole Assemblies as NO-Releasing Anticancer Agents.Pharmaceutics · 2025Article
- Theoretical studies on anhydride dynamic covalent bond exchange mechanisms.Communications chemistry · 2025Article
- Synthesis of PChemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Beyond Friedel-Crafts: Spontaneous and Fluoride-Catalyzed Acylation of 2-(Trialkylsilyl)pyridines.Organic letters · 2025Article
- Desulfinative Cross-Coupling as a Method to Overcome Problematic Suzuki-Miyaura Reactions of Pharmaceutically Relevant Heteroaromatic Boronates.ACS medicinal chemistry letters · 2025Review
- Pnictogen bonding enabled photosynthesis of chiral selenium-containing pyridines from pyridylphosphonium salts.Fundamental research · 2025Article
- Direct carbonyl reductive functionalizations by diphenylphosphine oxide.Science advances · 2025Article
- Mechanistic insights into the base-mediated deuteration of pyridyl phosphonium and ammonium salts.RSC advances · 2025Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
Abstract
Heterobiaryls composed of pyridine and diazine rings are key components of pharmaceuticals and are often central to pharmacological function. We present an alternative approach to metal-catalyzed cross-coupling to make heterobiaryls using contractive phosphorus C-C couplings, also termed phosphorus ligand coupling reactions. The process starts by regioselective phosphorus substitution of the C-H bonds para to nitrogen in two successive heterocycles; ligand coupling is then triggered via acidic alcohol solutions to form the heterobiaryl bond. Mechanistic studies imply that ligand coupling is an asynchronous process involving migration of one heterocycle to the ipso position of the other around a central pentacoordinate P(V) atom. The strategy can be applied to complex drug-like molecules containing multiple reactive sites and polar functional groups, and also enables convergent coupling of drug fragments and late-stage heteroarylation of pharmaceuticals.
Indexed as
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.