Three‐Component Radical Cross‐Coupling: Asymmetric Vicinal Sulfonyl‐Esterification of Alkenes Involving Sulfur Dioxide

Abstract: A novel catalytic system for radical cross‐coupling reactions based on copper and chiral Pyridyl‐bis (imidazole) (PyBim) ligands is described. It overcomes the challenges of chemoselectivity and enantioselectivity, achieving a highly enantioselective vicinal sulfonyl‐esterification reaction of alkenes involving sulfur dioxide. This strategy involves the use of earth‐abundant metal catalyst, mild reaction conditions, a broad range of substrates (84 examples), high yields (up to 97% yield), and exceptional control over enantioselectivity. The reaction system is compatible with different types of radical precursors, including O‐acylhydroxylamines, cycloketone oxime esters, aryldiazonium salts, and drug molecules. Chiral ligand PyBim is identified as particularly effective in achieving the desired high enantioselectivity. Mechanistic studies reveal that copper/PyBim system plays a vital role in C─O coupling, employing an outer‐sphere model. In addition, the side arm effect of ligand is observed.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Three‐Component Radical Cross‐Coupling: Asymmetric Vicinal Sulfonyl‐Esterification of Alkenes Involving Sulfur Dioxide ; day:26 ; month:03 ; year:2024 ; extent:10 ; Advanced science ; (26.03.2024) (gesamt 10)

Contributors, Places and Time

• Creator: Chang, Zhiqian ; Zhang, Xuemei ; Lv, Haiping ; Sun, Haotian ; Lian, Zhong

Further information

• DOI: 10.1002/advs.202309069
• URN: urn:nbn:de:101:1-2024032713201227049401
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 14.08.2025, 11:01 AM CEST