Synthesis, characterization and theoretical and fluorescence emission microscopy studies of new Pd/Pt–cyclopropa[60]fullerene complexes: Application of Taguchi method for optimization of parameters in Suzuki–Miyaura reaction

Abstract

The reactions of unsymmetric phosphorus ylides of the type [Ph2P(CH2)nPPh2C(H)C(O)C6H4‐p‐CN] (n = 1 (Y1); n = 2 (Y2)) with C60 and M(dba)2 (M = Pd or Pt; dba = dibenzylideneacetone) are reported. Based on the various coordination modes of these ylides in complexation, the following new Pd/Pt–cyclopropa[60]fullerene complexes were obtained: P,C‐coordinated [(η2‐C60)Pd(κ2‐Y1)] (1) and [(η2‐C60)Pt(κ2‐Y1)] (2) complexes and P‐coordinated [(η2‐C60)Pd(Y2)2] (3) and [(η2‐C60)Pt(Y2)2] (4) complexes. These compounds were characterized using Fourier transform infrared, UV–visible and NMR (1H, 13C and 31P) spectroscopies and scanning electron microscopy. Furthermore, cytotoxicity studies showed that nanoparticles of these complexes can be used as non‐toxic labels for cellular imaging application. Also energy decomposition analysis results revealed that the percentage contribution of ΔEelec in total interaction energy is considerably larger than that of ΔEorb. Thus, in all complexes the (η2‐C60)M(Y1) bond is considerably more electrostatic in nature than the (η2‐C60)M(Y1) bond. Finally, by application of the Taguchi method for optimization of parameters in Suzuki–Miyaura reaction, the catalytic activity of Pd complexes 1 and 3 was investigated in the cross‐coupling reaction of various aryl chlorides with phenylboronic acid. According to analysis of variance results, solvent has the highest F value and it has high contribution percentage (36.75%) to the yield of Suzuki–Miyaura reaction.

Carbon‐Derived Supports for Palladium Nanoparticles as Catalysts for Carbon‐Carbon Bonds Formation

“…The complex has also the beneficial effects of heterogeneous catalysts because it can be recycled during five cycles in the Heck reaction of chlorobenzene with styrene at rt with yields in the range of 90 to 81 %. The same group have used the same palladacycle and also platinacycle as catalysts in the Suzuki reaction of aryl chlorides with phenylboronic acid . The reactions were carried out with K 2 CO 3 as a base in DMF at 130 °C.…”

Structure and Dynamic Rearrangements of the Pt2dba3 and Pd2dba3 Complexes in Solution

“…Pt 2 dba 3 is a widely utilized source of Pt species for catalysis and a precursor of Pt compounds. Many nanoscale , and bimetallic , catalysts, electrocatalysts, − functional materials, − homogeneous catalysts, − and metal complexes for materials science − can be generated from these materials. Moreover, there are examples of direct use of Pt 2 dba 3 as a catalyst. − However, despite the significance of this compound, its structure has not yet been fully established.…”

Examination of Pt2dba3 as a “cocktail”-type catalytic system for alkene and alkyne hydrosilylation reactions

“…Tris(dibenzylideneacetone)diplatinum Pt 2 dba 3 is widely applied as a platinum(0) source [54][55][56][57][58][59][60][61][62] and, in contrast to Karstedt's catalyst, is practically convenient and handy to use. It is a stable dark solid that can be obtained from available reagents such as tetrachloroplatinate(II) and hexachloroplatinic(IV) acid.…”