Search results for "C-C coupling"

Electroactive polymeric material with condensed structure on the basis of magnesium(II) polyporphine

2011

International audience; Previous publication of the authors presented evidences that electroch emical oxidation of Mg(II) porphine (fully unsubstituted porphyrin, MgP) in acetonitrile (AN) at a very low potential leads to deposition of films at electrode surface corresponding to typical electroactive polymers, with their reversible transition betwee n the electronconducting and insulating states depending on the electrode potential/oxidation level ("film of type I"). It is demonstrated in the actual publication that these films in contact with a monomer-free solution are subject to an irreversible transformation to quite a different material ("film of type II") under the influence of a high…

Palladium Supported on Cross-Linked Imidazolium Network on Silica as Highly Sustainable Catalysts for the Suzuki Reaction under Flow Conditions

2013

Highly cross-linked imidazolium-based materials, obtained by radical oligomerization of bis-vinylimidazolium salts in the presence of 3-mercaptopropyl-modified silica gel, were used as supports for palladium catalysts. Thanks to the high imidazolium loading these materials were able to support a high amount of the metal (10 wt%). Such materials were characterized by several techniques (13C magic angle spinning nuclear magnetic resonance, the Brunauer-Emmett-Teller technique, X-ray photoelectron spectroscopy, and transmission electron microscopy). The palladium catalysts displayed good activity allowing the synthesis of several biphenyl compounds in high yields working with only 0.1 mol% of …

An E-Factor Minimized Protocol for a Sustainable and Efficient Heck Reaction in Flow

2014

A highly sustainable and waste-minimized protocol for Heck coupling has been defined. Optimal conditions have been defined by exploiting a heterogeneous catalyst based on supported ionic liquid-like phases featuring high Pd loading (10 wt %) and by optimizing its efficiency in a recoverable green reaction medium (acetonitrile/water azeotrope). Pure products 4a–l and 6a–h have been isolated chromatography-free in high yields (74–99%) and with extremely low environmental factor (E-factor) values (2.3–5.0). With the application of flow technology, the selected heterogeneous base and Pd catalyst have been fully recovered and reused, and minimum palladium leaching allowed for isolation of the fi…

Catechol-Functionalized Carbon Nanotubes as Support for Pd Nanoparticles

2022

Carbon nanotubes have been covalently functionalized with catechol moieties through the formation of the corresponding aryl radicals obtained by reacting 4-aminocatechol with isoamyl nitrite. The functionalized multiwalled carbon nanotubes have been in turn used to immobilize Pd(II) ions on its surface forming catechol-Pd complexes, which were reduced to Pd nanoparticles (NPs). The so-obtained hybrid material has been characterized by means of thermogravimetric analysis coupled with differential scanning calorimetry (TGA-DSC), X-ray photoelectron spectroscopy (XPS) and transmission electron microscopy (TEM). This latter technique allowed to estimate the nanoparticle size (5.7 +/- 2.8 nm) wh…

DESIGN OF NOVEL IMIDAZOLIUM BASED NANOSTRUCTURES FOR SUSTAINABLE CATALYTIC APPLICATIONS

Highly Loaded Multi-Walled Carbon Nanotubes Non-Covalently Modified with a Bis-Imidazolium Salt and their Use as Catalyst Supports

2016

The surfaces of multi-walled carbon nanotubes (MWCNTs) were non-covalently modified using two bis-imidazolium dibromide derivatives having phenyl or pyrene groups. Due to the presence of the two pyrene groups the bis(pyren-1-ylmethylimidazolium) dibromide derivative was immobilised at a loading of about 15-16 wt %, whereas only <3 wt % of the phenyl derivative was immobilised. The presence of the two imidazolium cations helped the immobilisation of tetrachloropalladate ions after exchange with bromide ions. Tetrachloropalladate was used as pre-catalyst in several Suzuki-Miyaura carbon-carbon cross-coupling reactions in water or water/ethanol at 50 °C in only 0.1 mol % and compared with the …

Carbocatalytic Oxidative Dehydrogenative Couplings of (Hetero)Aryls by Oxidized Multi‐Walled Carbon Nanotubes in Liquid Phase

2019

HNO3-oxidized carbon nanotubes catalyze oxidative dehydrogenative (ODH) carbon-carbon bond formation between electron-rich (hetero)aryls with O-2 as a terminal oxidant. The recyclable carbocatalytic method provides a convenient and an operationally easy synthetic protocol for accessing various benzofused homodimers, biaryls, triphenylenes, and related benzofused heteroaryls that are highly useful frameworks for material chemistry applications. Carbonyls/quinones are the catalytically active site of the carbocatalyst as indicated by model compounds and titration experiments. Further investigations of the reaction mechanism with a combination of experimental and DFT methods support the compet…

Antiproliferative agents that interfere with the cell cycle at the G(1)-->S transition: further development and characterization of a small library o…

2008

In this continuation of our research on derivatives containing the stilbene privileged structure or that are derived from it, we report the results of further studies carried out on the previously initiated collection of compounds. We used a parallel synthetic approach to rapidly obtain small sets of compounds and started the annotation of the library in progress by calculating some physicochemical properties to be eventually correlated with biological activities. A pharmacophore for the antiproliferative activity was also built to summarize the features of the library. We evaluated the antiproliferative and pro-apoptotic activities of all compounds as well as the cell-cycle effects of some…

Fullerene-ionic-liquid conjugates: a new class of hybrid materials with unprecedented properties.

2015

A modular approach has been followed for the synthesis of a series of fullerene-ionic-liquid (IL) hybrids in which the number of IL moieties (two or twelve), anion, and cation have been varied. The combination of C60 and IL give rise to new unique properties in the conjugates such as solubility in water, which was higher than 800 mg mL(-1) in several cases. In addition, one of the C60 -IL hybrids has been employed for the immobilization of palladium nanoparticles through ion exchange followed by reduction with sodium borohydride. Surprisingly, during the reduction several carbon nanostructures were formed that comprised nano-onions and nanocages with few-layer graphene sidewalls, which have…

Proximity Effect using a Nanocage Structure: Polyhedral Oligomeric Silsesquioxane-Imidazolium Tetrachloro- palladate Salt as a Precatalyst for the Su…

2016

A polyhedral oligomeric silsesquioxane-imidazolium tetrachloropalladate salt (POSS-Imi-PdCl4) was prepared by the reaction of a polyhedral oligomeric silsesquioxane-imidazolium chloride salt (POSS-Imi-Cl) with PdCl2 and used as a pre-catalyst for the Suzuki-Miyaura reaction in water at 100 °C at a low loading (0.08-0.16 mol %). Biphenyl compounds were isolated in high to excellent yields. A comparison of the POSS-based catalyst with the corresponding catalyst without the nanocage structure (i.e., 1-butyl-3-methylimidazolium tetrachloropalladate) highlighted the role of the POSS structure to reach higher yields in the Suzuki-Miyaura reaction. This result is ascribed to a proximity effect of …