New approach to synthesis of tri(1-naphthyl)phosphine (Np 3 P) and its application for design of new Pd(II) and Cu(I) complexes are reported. This phosphine has been prepared in 32% yield through exhaustive P–H arylation of РН 3 with 1-chloronaphthalene in the superbasic t-BuOK/DMSO system at 70 °C. The Np 3 P was found to readily reacts with chloro-bridged dimers, [(κ 2 -C,N)Pd(μ-Cl)] 2 (κ 2 -C,N = PhCH 2 NMe 2 (2a) or FcCH 2 NMe 2 (2b), to give new mononuclear palladacycles [(κ 2 -C,N)Pd(Np 3 P)Cl] (3, 4), in which metal has a square-planar geometry. These complexes show good catalytic activity in the Sonogashira reaction under low catalyst loadings (2 mol% Pd) and relatively mild conditions. We also synthesized and characterized first Cu(I) complex with Np 3 P, namely, [Cu(phen)(Np 3 P)I], that exhibits red emission (λ max = 650 nm) at room temperature.
- Sonogashira coupling
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Inorganic Chemistry
- Materials Chemistry