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Palladium-Catalyzed Coupling of Aryl Chlorides with Secondary Phosphines to Construct Unsymmetrical Tertiary Phosphines

Yuxuan Xiao, Xun Yang, Haiyan Li, Ying Yin, Jiahui Du, Jing Liang, Wengui Duan, Lin Yu

2024Organic Letters17 citationsDOI

Abstract

The functionalization of the C-Cl bond in unactivated aryl chlorides under mild conditions presents a significant challenge. We disclose a general protocol for constructing both partially and entirely unsymmetrical tertiary phosphines through the Pd/keYPhos-catalyzed coupling of aryl chlorides with secondary phosphines under mild conditions. The reaction exhibits excellent functional group tolerance and broad substrate scopes. Furthermore, the rapid synthesis of ligands and luminescent compound sTPPs, alongside gram-scale systhesis, demonstrates the practical applicability of this method.

Topics & Concepts

ChemistryArylPalladiumCatalysisCoupling (piping)Medicinal chemistryConstruct (python library)Organic chemistryCombinatorial chemistryAlkylMechanical engineeringProgramming languageEngineeringComputer scienceCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and CatalysisSulfur-Based Synthesis Techniques