Construction of Axially Chiral Biaryl Sulfonamides by Palladium/Chiral Norbornene Cooperative Catalysis

Abstract Aryl sulfonamide scaffold is a privileged pharmacophore, and is prevalent in pharmaceuticals. Existing aryl sulfonamide‐based pharmaceuticals are either achiral or limited to central chirality, leaving the potential of axially chiral biaryl sulfonamides underexplored. Beyond therapeutic applications, these structures also serve as versatile chiral ligands and catalysts. However, their catalytic asymmetric synthesis remains challenging, with prior methods predominantly accessing N‐side axially chiral variants, while S‐side analogues are scarcely reported. To date, only one approach based on asymmetric Suzuki‐Miyaura cross‐coupling was reported by Tang and co‐workers. We herein report a highly efficient method for the enantioselective synthesis of axially chiral biaryl sulfonamides via palladium/chiral norbornene cooperative catalysis, exploiting readily available aryl iodides, bulky 2‐bromobenzenesulfonamides and olefins as the reactants. This approach demonstrates broad substrate scope, excellent enantioselectivities, step economy, and scalability.

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Publication Details

Journal
ChemCatChem
Published
2025-04-27
DOI
https://doi.org/10.1002/cctc.202500560
Citations
1
Primary Topic
Axial and Atropisomeric Chirality Synthesis
Type
article
Field-Weighted Citation Impact
0.94
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article

Construction of Axially Chiral Biaryl Sulfonamides by Palladium/Chiral Norbornene Cooperative Catalysis

Qianghui Zhou, Ziyang Cui
1 citations
ChemCatChem
Axial and Atropisomeric Chirality Synthesis
0.94
article

Construction of Axially Chiral Biaryl Sulfonamides by Palladium/Chiral Norbornene Cooperative Catalysis

Qianghui Zhou, Ziyang Cui
article en
1 citations

Abstract

Abstract Aryl sulfonamide scaffold is a privileged pharmacophore, and is prevalent in pharmaceuticals. Existing aryl sulfonamide‐based pharmaceuticals are either achiral or limited to central chirality, leaving the potential of axially chiral biaryl sulfonamides underexplored. Beyond therapeutic applications, these structures also serve as versatile chiral ligands and catalysts. However, their catalytic asymmetric synthesis remains challenging, with prior methods predominantly accessing N‐side axially chiral variants, while S‐side analogues are scarcely reported. To date, only one approach based on asymmetric Suzuki‐Miyaura cross‐coupling was reported by Tang and co‐workers. We herein report a highly efficient method for the enantioselective synthesis of axially chiral biaryl sulfonamides via palladium/chiral norbornene cooperative catalysis, exploiting readily available aryl iodides, bulky 2‐bromobenzenesulfonamides and olefins as the reactants. This approach demonstrates broad substrate scope, excellent enantioselectivities, step economy, and scalability.

ChemCatChemVol. 17(13)
Wuhan University (CN), Ministry of Education (IR)
Openalex Percentile: Top 27%
Axial and Atropisomeric Chirality Synthesis
0.94
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