Palladium-catalyzed air-based oxidative coupling of arylboronic acids with H-phosphine oxides leading to aryl phosphine oxides?

Organic & Biomolecular Chemistry Pub Date: 2014-02-26 DOI: 10.1039/C3OB42470G

Abstract

We present a novel and highly efficient methodology that allows for the construction of C–P bonds via the palladium-catalyzed air-based oxidative coupling of various commercially available arylboronic acids with easily oxidized H-phosphine oxides leading to valuable aryl phosphine oxides, particularly triarylphosphine oxides, with the use of air as the green oxidant, broad substrate applicability and good to excellent yields. The described catalytic system should be an efficient complement to the Chan–Lam type reaction and be useful in synthetic programs.

Graphical abstract: Palladium-catalyzed air-based oxidative coupling of arylboronic acids with H-phosphine oxides leading to aryl phosphine oxides
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