ArticleChemical science2017
Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides.
Article in Chemical science, 2017. 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, 93 citations in OpenAlex.
- Versatile Palladium-Catalyzed C-H Arylation of Fluoroarenes with 2-Chloropyridine Derivatives.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Electrochemical functionalization of pyridines.Chemical science · 2026Review
- Desulfinative Cross-Coupling as a Method to Overcome Problematic Suzuki-Miyaura Reactions of Pharmaceutically Relevant Heteroaromatic Boronates.ACS medicinal chemistry letters · 2025Review
- Synthesis of CThe Journal of organic chemistry · 2024Article
- Copper-Catalyzed Synthesis of Masked (Hetero)Aryl Sulfinates.Organic letters · 2024Article
- Recent Progress on the Synthesis of Bipyridine Derivatives.Molecules (Basel, Switzerland) · 2024Review
- Discovery of Novel Dual Adenosine APharmaceuticals (Basel, Switzerland) · 2022Article
- Reductant-Free Cross-Electrophile Synthesis of Di(hetero)arylmethanes by Palladium-Catalyzed Desulfinative C-C Coupling.Angewandte Chemie (International ed. in English) · 2022Article
- Functional group divergence and the structural basis of acridine photocatalysis revealed by direct decarboxysulfonylation.Chemical science · 2022Article
- Visible Light-Driven, Gold(I)-Catalyzed Preparation of Symmetrical (Hetero)biaryls by Homocoupling of Arylazo Sulfones.The Journal of organic chemistry · 2022Article
- A General, Multimetallic Cross-Ullmann Biheteroaryl Synthesis from Heteroaryl Halides and Heteroaryl Triflates.Journal of the American Chemical Society · 2021Article
- Synthesis of Bis-heteroaryls Using Grignard Reagents and Pyridylsulfonium Salts.Organic letters · 2021Article
- Photoinduced C(spChemical science · 2021Article
- Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions.Angewandte Chemie (International ed. in English) · 2021Article
- The 2-Pyridyl Problem: Challenging Nucleophiles in Cross-Coupling Arylations.Angewandte Chemie (International ed. in English) · 2021Review
- Synthesis and Anticancer Activity of Mitotic-Specific 3,4-Dihydropyridine-2(1International journal of molecular sciences · 2021Article
- Z-Selective Dienylation Enables Stereodivergent Construction of Dienes and Unravels a Ligand-Driven Mechanistic Dichotomy.ACS catalysis · 2021Article
- Organic-photoredox-catalyzed three-component sulfonylative pyridylation of styrenes.RSC advances · 2020Article
- Mechanistic Studies of the Palladium-Catalyzed Desulfinative Cross-Coupling of Aryl Bromides and (Hetero)Aryl Sulfinate Salts.Journal of the American Chemical Society · 2020Article
- Scope and limitation of propylene carbonate as a sustainable solvent in the Suzuki-Miyaura reaction.RSC advances · 2019Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 3 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Pyridine rings are ubiquitous in drug molecules; however, the pre-eminent reaction used to form carbon-carbon bonds in the pharmaceutical industry, the Suzuki-Miyaura cross-coupling reaction, often fails when applied to these structures. This phenomenon is most pronounced in 2-substituted pyridines, and results from the difficulty in preparing, the poor stability of, and low efficiency in reactions of pyridine-2-boronates. We demonstrate that by replacing these boronates with pyridine-2-sulfinates, a cross-coupling process of unrivalled scope and utility is realized. The corresponding 3- and 4-substituted pyridine variants are also efficient coupling partners. In addition, we apply these sulfinates in a library format to the preparation of medicinally relevant derivatives of the drugs varenicline (Chantix) and mepyramine (Anthisan).
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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.