Electron-Rich Silicon Containing Phosphinanes for Rapid Pd-Catalyzed C-X Coupling Reactions

Kräh, Sabrina; Kachel, Iris und Trapp, Oliver (2022): Electron-Rich Silicon Containing Phosphinanes for Rapid Pd-Catalyzed C-X Coupling Reactions. In: Chemcatchem, Bd. 14, Nr. 16

Abstract

Palladium-catalyzed cross-coupling reactions are among the most useful and efficient methods for direct access to complex structures in organic synthesis. However, heteroatom-containing compounds can complicate such coupling reactions due to their competitive coordination with the palladium catalyst and electronic effects. As a result, good yields are often only obtained under harsher reaction conditions, such as high temperatures and long reaction times. Here the design of a highly active phosphine ligand is reported that provides excellent yields for C-N coupling reactions at ambient temperature. Incorporation of the phosphorus atom into a cyclohexane ring maintains the pyramidal structure of the phosphorus while reducing steric hindrance. This, and a silicon atom in the cyclohexane moiety, results in an electron-rich phosphinane ligand. This novel silicon containing SabPhos ligand can be obtained in excellent yields in a straightforward synthesis. In palladium catalyzed reactions, this ligand facilitates the coupling of a broad range of heteroaryl chlorides via C-C bonds with boronic acids and C-N bonds with secondary amines in excellent yields under mild conditions.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1867-3880
• Sprache: Englisch
• DFG: Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 491502892