ArticleJournal of the American Chemical Society2020
Mechanistic Studies of the Palladium-Catalyzed Desulfinative Cross-Coupling of Aryl Bromides and (Hetero)Aryl Sulfinate Salts.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 42 citations in OpenAlex.
- The influence of the substituent type and position on the topology of 2-D heterometallic sodium-palladium(ii) coordination networks with substituted nicotinate ligands.RSC advances · 2026Article
- Desulfinative Cross-Coupling as a Method to Overcome Problematic Suzuki-Miyaura Reactions of Pharmaceutically Relevant Heteroaromatic Boronates.ACS medicinal chemistry letters · 2025Review
- Heterocyclic Suzuki-Miyaura coupling reaction of metalla-aromatics and mechanistic analysis of site selectivity.Chemical science · 2023Article
- Amine-Catalyzed Copper-Mediated C-H Sulfonylation of Benzaldehydes via a Transient Imine Directing Group.Angewandte Chemie (International ed. in English) · 2022Article
- Reductant-Free Cross-Electrophile Synthesis of Di(hetero)arylmethanes by Palladium-Catalyzed Desulfinative C-C Coupling.Angewandte Chemie (International ed. in English) · 2022Article
- Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions.Angewandte Chemie (International ed. in English) · 2021Article
- Zirconium-Redox-Shuttled Cross-Electrophile Coupling of Aromatic and Heteroaromatic Halides.Chem · 2021Article
- The 2-Pyridyl Problem: Challenging Nucleophiles in Cross-Coupling Arylations.Angewandte Chemie (International ed. in English) · 2021Review
- Palladium-Catalyzed Sulfinylation of Aryl- and Alkenylborons with Sulfinate Esters.Organic letters · 2021Article
- Z-Selective Dienylation Enables Stereodivergent Construction of Dienes and Unravels a Ligand-Driven Mechanistic Dichotomy.ACS catalysis · 2021Article
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Authors and funding
5 authors at 3 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Pyridine and related heterocyclic sulfinates have recently emerged as effective nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with (hetero)aryl halides. These sulfinate reagents are straightforward to prepare, stable to storage and coupling reaction conditions, and deliver efficient reactions, thus offering many advantages, compared to the corresponding boron-derived reagents. Despite the success of these reactions, there are only scant details of the reaction mechanism. In this study, we use structural and kinetic analysis to investigate the mechanism of these important coupling reactions in detail. We compare a pyridine-2-sulfinate with a carbocyclic sulfinate and establish different catalyst resting states, and turnover limiting steps, for the two classes of reagent. For the carbocyclic sulfinate, the aryl bromide oxidative addition complex is the resting state intermediate, and transmetalation is turnover-limiting. In contrast, for the pyridine sulfinate, a chelated Pd(II) sulfinate complex formed post-transmetalation is the resting-state intermediate, and loss of SO
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