ArticleJournal of the American Chemical Society2013
Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles: substrate scope and mechanistic investigation.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 56 papers.
What it found
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Who cites it
56 citing papers in PubMed, 1 citations in OpenAlex.
- DiploPhos: A Hemilabile Bisphosphine for Sterically Hindered Ni-Catalyzed Suzuki-Miyaura Couplings.ACS catalysis · 2026Article
- Enantioselective Rh-catalyzed addition of indoles to enones and the key role of the free N-H group with acyclic enones.Chemical science · 2026Article
- Synthesis and Biological Evaluation of 4‑Bromo-ACS omega · 2026Article
- New Indazole Derivatives as Potential Scaffolds for the Development of Anticancer, Antiviral, and Anti-tuberculosis Chemotherapeutic Compounds.Current medicinal chemistry · 2026Article
- Solvent Sustainability in Drug Discovery: Where Are We Now, and How Can We Improve?Journal of medicinal chemistry · 2025Review
- Article
- Pd-Catalyzed O-Arylation of Phenols Mediated by a Weak, Soluble Organic Base: Methodology, Mechanism, and Compatibility with Enabling Technologies.Journal of the American Chemical Society · 2025Article
- Considerations in Pursuing Reaction Scope Generality.Angewandte Chemie (International ed. in English) · 2025Review
- Design and synthesis of novel small molecules targeting the Kv1.3 voltage-gated potassium ion channel.Scientific reports · 2025Article
- Automated Iterative N─C and C─C Bond Formation.Angewandte Chemie (International ed. in English) · 2025Article
- Functionalized in Triplicate: A Ring-By-Ring Approach to Tailored Prodiginine Derivatives for Site-Specific Conjugation Through Click Chemistry.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Efficient Nickel Precatalysts for Suzuki-Miyaura Cross-Coupling of Aryl Chlorides and Arylboronic Acids Under Mild Conditions.Angewandte Chemie (International ed. in English) · 2025Article
- Anti-Diabetic Activities and Molecular Docking Studies of Aryl-Substituted Pyrazolo[3,4-b]pyridine Derivatives Synthesized via Suzuki Cross-Coupling Reaction.Pharmaceuticals (Basel, Switzerland) · 2024Article
- Development of di-arylated 1,2,4-triazole-based derivatives as therapeutic agents against breast cancer: synthesis and biological evaluation.RSC medicinal chemistry · 2024Article
- Halide Salts Alleviate TMSOK Inhibition in Suzuki-Miyaura Cross-Couplings.ACS catalysis · 2024Article
- Phase transfer catalysts shift the pathway to transmetalation in biphasic Suzuki-Miyaura cross-couplings.Nature communications · 2024Article
- Enabling synthesis in fragment-based drug discovery (FBDD): microscale high-throughput optimisation of the medicinal chemist's toolbox reactions.RSC medicinal chemistry · 2023Article
- C-C Bond Formation Reaction Catalyzed by a Lithium Atom: Benzene-to-Biphenyl Coupling.ACS omega · 2023Article
- Pyrazole-based lamellarin O analogues: synthesis, biological evaluation and structure-activity relationships.RSC advances · 2023Article
- Structure-Reactivity Relationships of Buchwald-Type Phosphines in Nickel-Catalyzed Cross-Couplings.Journal of the American Chemical Society · 2022Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles using precatalysts P1 or P2 is reported. The procedure allows for the reaction of variously substituted indazole, benzimidazole, pyrazole, indole, oxindole, and azaindole halides under mild conditions in good to excellent yields. Additionally, the mechanism behind the inhibitory effect of unprotected azoles on Pd-catalyzed cross-coupling reactions is described based on evidence gained through experimental, crystallographic, and theoretical investigations.
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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.