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Copper‐Catalyzed Dynamic Kinetic Asymmetric P−C Coupling of Secondary Phosphine Oxides and Aryl Iodides

Jie Kang, Kang Ding, Si‐Mu Ren, Bo Su

2023Angewandte Chemie International Edition57 citationsDOIOpen Access PDF

Abstract

Transition-metal-catalyzed enantioselective P-C cross-coupling of secondary phosphine oxides (SPOs) is an attractive method for synthesizing P-stereogenic phosphorus compounds, but the development of such a dynamic kinetic asymmetric process remains a considerable challenge. Here we report an unprecedented highly enantioselective dynamic kinetic intermolecular P-C coupling of SPOs and aryl iodides catalyzed by copper complexes ligated by a finely modified chiral 1,2-diamine ligand. The reaction tolerates a wide range of SPOs and aryl iodides, affording P-stereogenic tertiary phosphine oxides (TPOs) in high yields and with good enantioselectivity (average 89.2 % ee). The resulting enantioenriched TPOs were transformed into structurally diverse P-chiral scaffolds, which are highly valuable as ligands and catalysts in asymmetric synthesis.

Topics & Concepts

StereocenterPhosphineEnantioselective synthesisArylCatalysisChemistryLigand (biochemistry)Kinetic resolutionCopperCombinatorial chemistryMedicinal chemistryOrganic chemistryReceptorBiochemistryAlkylAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisOrganoboron and organosilicon chemistry
Copper‐Catalyzed Dynamic Kinetic Asymmetric P−C Coupling of Secondary Phosphine Oxides and Aryl Iodides | Litcius