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Relevant academic research and scientific papers

Highly active, selective, and reusable RuO2/SWCNT catalyst for heck olefination of aryl halides

Very fine RuO2 nanoparticles (RuO2NPs) with a mean diameter of about 0.9 nm were decorated on single-walled carbon nanotubes (SWCNTs) by a straightforward "dry synthesis" method. TEM images and the Raman spectrum of the resultant material (RuO2/SWCNT) revealed excellent adhesion and homogeneous dispersion of the RuO2NPs on anchoring sites of the SWCNTs. The surface area of RuO2/SWCNT was found to be 416 m2 g-1. The SEM-EDS results showed that the weight percentage of Ru in RuO2/SWCNT was 13.8%. The oxidation state of Ru in RuO2/SWCNT was +4, as confirmed by XPS and XRD analyses. After the complete characterization, a 0.9 mol % loading of RuO 2/SWCNT was used as a nanocatalyst for the Heck olefination of a wide range of aryl halides to yield products in excellent yields with good turnover numbers and turnover frequencies. Less reactive bromo-and chloroarenes were also used for the formation of coupled products in good yields. RuO 2/SWCNT is regioselective, chemoselective, heterogeneous in nature, and reusable. The stability of RuO2/SWCNT was also studied by means of TEM, ICP-MS, SEM-EDS, and XPS analyses.

METHODS OF ARENE ALKENYLATION

The present disclosure provides for a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. For example, the present disclosure provides for method of making arenes or substituted arenes, in particular stilbene and stilbene derivatives, from a reaction of an optionally substituted arene and/or optionally substituted styrene. The reaction includes a Rh catalyst or Rh pre-catalyst material and an oxidant, where the Rh catalyst or Rh catalyst formed Rh pre-catalyst material selectively functionalizes CH bond on the arene compound (e.g., benzene or substituted benzene).

Synthesis of Stilbenes by Rhodium-Catalyzed Aerobic Alkenylation of Arenes via C-H Activation

Arene alkenylation is commonly achieved by late transition metal-mediated C(sp2)-C(sp2) cross-coupling, but this strategy typically requires prefunctionalized substrates (e.g., with halides or pseudohalides) and/or the presence of a directing group on the arene. Transition metal-mediated arene C-H activation and alkenylation offers an alternative method to functionalize arene substrates. Herein, we report a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. The reaction is successful with several functional groups on both the arene and the olefin including fluoride, chloride, trifluoromethyl, ester, nitro, acetate, cyanide, and ether groups. Reactions of monosubstituted arenes are selective for alkenylation at the meta and para positions, generally with approximately 2:1 selectivity, respectively. Resveratrol and (E)-1,2,3-trimethoxy-5-(4-methoxystyryl)benzene (DMU-212) are synthesized by this single-step approach in high yield. Comparison with palladium catalysis showed that rhodium catalysis is more selective for meta-functionalization for monosubstituted arenes and that the Rh catalysis has better tolerance of halogen groups.

The use of palladium nanoparticles supported on graphene oxide in the Mizoroki-Heck reaction

We have developed a convenient single-step method for producing palladium nanoparticles on the surface of graphene oxide by reducing palladium chloride with NaBH4. According to transmission electron microscopy data, palladium nanoparticles have