Abstract:The Suzuki-Miyaura reaction (SMR), involving the coupling of an organoboron reagent and an organic halide or pseudo-halide in the presence of a palladium or nickel catalyst and a base, has arguably become one of most utilized tools for the construction of a C-C bond. This review intends to be general account of all types of catalytic systems, new coupling partners and applications, including the
We report on the synthesis, characterization,
and stability studies
of new titanocene complexes containing a methyl group and a carboxylate
ligand (mba = −OC(O)-p-C6H4-S−) bound to gold(I)–N-heterocyclic carbene
fragments through the thiolate group: [(η5-C5H5)2TiMe(μ-mba)Au(NHC)]. The cytotoxicities
of the heterometallic compounds along with those of novel monometallic
gold–N-heterocyclic carbene precursors [(NHC)Au(mbaH)] have
been evaluated against renal, prostate, colon, and breast cancer cell
lines. The highest activity and selectivity and a synergistic effect
of the resulting heterometallic species was found for the prostate
and colon cancer cell lines. The colocalization of both titanium and
gold metals (1:1 ratio) in PC3 prostate cancer cells was demonstrated
for the selected compound 5a, indicating the robustness
of the heterometallic compound in vitro. We describe here preliminary
mechanistic data involving studies on the interaction of selected
mono- and bimetallic compounds with plasmid (pBR322) used as a model
nucleic acid and the inhibition of thioredoxin reductase in PC3 prostate
cancer cells. The heterometallic compounds, which are highly apoptotic,
exhibit strong antimigratory effects on the prostate cancer cell line
PC3.
The reactions between a series of thiophene-based imines with [(η(6)-C(6)H(6))RuCl(μ-Cl)](2), in a basic medium, and in MeCN give a family of ruthenacycles of stoichiometry [Ru(C^N)(NCMe)(4)]PF(6) (C^N = orthometalated thiopheneimine). In these species, the C-H activation process is produced in most cases at the thiophene ring. When two C-H bonds are competing (thiophene vs aryl), the cyclometalation can be driven regioselectively to the thiophene unit or to the aryl ring as a function of the location of the iminic C=N bond. Cyclometalation can also be oriented to positions 2 or 3 of the thiophene depending on the situation of the imine in the heterocycle (3 or 2, respectively). In all studied cases, the η(6)-C(6)H(6) ligand was substituted by acetonitrile. The X-ray structures of two representative complexes have been determined. These thiophene-based metallacycles react with iodine under very mild conditions affording, after hydrolysis, substituted 3-iodo-2-formyl(benzo)thiophenes or substituted 2-iodo-3-formyl(benzo)thiophenes, as a function of the organometallic precursor.
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