Issue 3, 2025

Axially chiral biaryls via rhodium-catalyzed atroposelective C–H sulfenylation and selenylation

Abstract

Transition metal-catalyzed atroposelective C–H activation has become an efficient approach for the rapid construction of functionalized axially chiral biaryls, but remains challenging in the synthesis of chalcogenated axially chiral biaryls due to the strong binding affinity between the chalcogen and metal center. Herein, we report an efficient rhodium-catalyzed atroposelective C–H chalcogenation of biaryls with readily accessible disulfides and diselenides. The reaction occurs in the presence of a silver salt as a chalcophile to regenerate the active chiral rhodium catalyst. This protocol features a broad scope and mild conditions, affording a series of axially chiral biaryl sulfides and selenides in excellent yields and enantioselectivities.

Graphical abstract: Axially chiral biaryls via rhodium-catalyzed atroposelective C–H sulfenylation and selenylation

Supplementary files

Article information

Article type
Research Article
Submitted
06 Nov 2024
Accepted
22 Nov 2024
First published
27 Nov 2024

Org. Chem. Front., 2025,12, 816-823

Axially chiral biaryls via rhodium-catalyzed atroposelective C–H sulfenylation and selenylation

Y. Wang, S. Yu and X. Li, Org. Chem. Front., 2025, 12, 816 DOI: 10.1039/D4QO01905A

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