ArticleJournal of the American Chemical Society2023
sSPhos: A General Ligand for Enantioselective Arylative Phenol Dearomatization via Electrostatically-Directed Palladium Catalysis.
Article in Journal of the American Chemical Society, 2023. 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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10 citing papers in PubMed, 31 citations in OpenAlex.
- An Enantioselective Alkene Aminoarylation to Form Chiral Indolines via Electrostatically-Directed Palladium Catalysis.Angewandte Chemie (International ed. in English) · 2026Article
- Optimization of a Resolution Process Allowing Access to Both Enantiomers of the Versatile Chiral Phosphine Ligand sSPhos on Scale.Organic process research & development · 2026Article
- First total synthesis of (±)-spirobroussonin B via electromediated oxidative coupling for constructing spirodienone ring.Natural products and bioprospecting · 2026Article
- Atroposelective Suzuki-Miyaura Coupling to Form 2-Amino-2'-Hydroxybiphenyls Enabled by sRuPhos.Angewandte Chemie (International ed. in English) · 2026Article
- Chiral Hydrogen-Bond Donor and Gold(I) Cocatalysis Enables Enantioselective Dearomative Spirocyclization of Naphthols.Journal of the American Chemical Society · 2025Article
- Enantioselective Formal Synthesis of (-)-Aflatoxin BOrganic letters · 2025Article
- Design Approaches That Utilize Ionic Interactions to Control Selectivity in Transition Metal Catalysis.Chemical reviews · 2025Review
- Substrate NOBINAc ligand affinity for PdChemical science · 2025Article
- Intermolecular Asymmetric Arylative Dearomatization of 1-Naphthols.Journal of the American Chemical Society · 2024Article
- Application of sSPhos as a Chiral Ligand for Palladium-Catalyzed Asymmetric Allylic Alkylation.Organic letters · 2024Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Arylative phenol dearomatization affords complex, cyclohexanone-based scaffolds from simple starting materials, and asymmetric versions allow access to valuable enantioenriched structures. However, bespoke chiral ligands must typically be identified for each new scaffold variation. We have addressed this limitation by applying the concept of electrostatically-directed palladium catalysis whereby the chiral sulfonated ligand sSPhos engages in electrostatic interactions with a phenolate substrate via its associated alkali metal cation. This approach allows access to highly enantioenriched spirocyclohexadienones, a process originally reported by Buchwald and co-workers in a predominantly racemic manner. In addition, sSPhos is proficient at forming two other distinct scaffolds, which had previously required fundamentally different chiral ligands, as well as a novel oxygen-linked scaffold. We envisage that the broad generality displayed by sSPhos will facilitate the expansion of this important reaction type and highlight the potential of this unusual design principle, which harnesses attractive electrostatic interactions.
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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.