Csp<sup>3</sup>−P<sup>III</sup> Bond Formation via Cross‐Coupling of Umpolung Carbonyls with Phosphine Halides Catalyzed by Nickel
Ruofei Cheng, Chao‐Jun Li
Abstract
bonds via the nickel-catalyzed cross-coupling of Umpolung carbonyls and phosphine chlorides is reported herein. This process leads to a series of alkylphosphines, which are characterized as sulfides or borane-phosphine complexes after undergoing further transformation with moderate to good yields. Invaluable free alkylphosphines can be easily obtained by desulfurization or deboration of the products. A possible mechanistic pathway is also discussed. This report represents the first example of using renewable carbonyls as latent organometallic reagent surrogates for cross-coupling with heteroatom electrophiles.
Topics & Concepts
UmpolungPhosphineChemistryElectrophileReagentHeteroatomBoraneNickelCatalysisHalideMedicinal chemistryOrganic chemistryCombinatorial chemistryAlkylNucleophileAsymmetric Hydrogenation and CatalysisOrganoboron and organosilicon chemistryCatalytic Cross-Coupling Reactions