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• 141-32-2 acrylic acid n-butyl ester 
• 5661-50-7 N-(phenoxy)acetamide 
• 64908-64-1 2-phenoxyisoindol-1,3-dione 
• 4846-21-3 O-phenylhydroxylamine 
• 108-95-2 phenol 
• 95-56-7 2-hydroxybromobenzene 
• 98-80-6 phenylboronic acid 
• 4107-40-8 N-Butyl-N'-phenoxyharnstoff 
• 65109-75-3 N-(phenoxy)-4-methylbenzenesulfonamide 
• 1315577-22-0 PhOSi(tBu)2OH 

Relevant academic research and scientific papers

S,O-Functionalized Metal-Organic Frameworks as Heterogeneous Single-Site Catalysts for the Oxidative Alkenylation of Arenes via C-H activation

Heterogeneous single-site catalysts can combine the precise active site design of organometallic complexes with the efficient recovery of solid catalysts. Based on recent progress on homogeneous thioether ligands for Pd-catalyzed C-H activation reactions, we here develop a scalable metal-organic framework-based heterogeneous single-site catalyst containing S,O-moieties that increase the catalytic activity of Pd(II) for the oxidative alkenylation of arenes. The structure of the Pd?MOF-808-L1 catalyst was characterized in detail via solid-state nuclear magnetic resonance spectroscopy, N2 physisorption, and high-angle annular dark field scanning transmission electron microscopy, and the structure of the isolated palladium active sites could be identified by X-ray absorption spectroscopy. A turnover frequency (TOF) of 8.4 h-1 was reached after 1 h of reaction time, which was 3 times higher than the TOF of standard Pd(OAc)2, ranking Pd?MOF-808-L1 among the most active heterogeneous catalysts ever reported for the nondirected oxidative alkenylation of arenes. Finally, we showed that the single-site catalyst promotes the oxidative alkenylation of a broad range of electron-rich arenes, and the applicability of this heterogeneous system was demonstrated by the gram-scale synthesis of industrially relevant products.

Thermo-responsive poly(N -isopropylacrylamide)- block -poly(ionic liquid) of pyridinium sulfonate immobilized Pd nanoparticles in C-C coupling reactions

A thermo-responsive poly(N-isopropylacrylamide)-block-poly(ionic liquid) (PNIPAM-b-PIL) of pyridinium-type was prepared. Initially, controlled synthesis of PNIPAM was performed via RAFT method. Subsequently, PNIPAM as macromolecular chain transfer agent (macro-CTA) was used for fabrication of PNIPAM-b-PIL through reaction with a synthesized IL monomer i.e. 4-vinyl pyridinium propane sulfonate. The Pd catalyst was produced throughout palladium nanoparticles' anchoring into this block copolymer. The catalyst was characterized using ICP, FT-IR, NMR, UV-Vis, TGA, XRD, SEM and EDX techniques. The catalyst's TEM image proved nearly fine dispersion of PdNPs with negligible agglomeration. The catalyst was used in the production of a variety of substituted alkenes and biaryl compounds (Heck and Suzuki coupling) in organic and aqueous media and under solvent free conditions. Additionally, the results signified extreme reusability of the catalyst with a simple recycling procedure.

Investigation of the Catalytic Activity of a 2-Phenylidenepyridine Palladium(II) Complex Bearing 4,5-Dicyano-1,3-bis(mesityl)imidazol-2-ylidene in the Mizoroki-Heck Reaction

The phenylidenepyridine (ppy) palladacycles [PdCl(ppy)(IMes)] (4) [IMes = 1,3-bis(mesityl)imidazol-2-ylidene] and [PdCl(ppy){(CN)2IMes}] (6) [(CN)2IMes = 4,5-dicyano-1,3-bis(mesityl)imidazol-2-ylidene] were prepared by facile two ste

Efficient palladium(II) precatalysts bearing 4,5-dicyanoimidazol-2-ylidene for the Mizoroki-Heck reaction

The new N-heterocyclic carbene (NHC) complex [PdCl2{(CN) 2IMes}(PPh3)] (2) ({(CN)2IMes}: 4,5-dicyano-1,3-dimesitylimidazol-2-ylidene) and the NHC palladacycle [PdCl(dmba){(CN)2IMes}] (3) (dmba: N,N-di

Efficient palladium(II) precatalysts bearing 4,5-dicyanoimidazol-2-ylidene for the mizoroki-heck reaction

The new N-heterocyclic carbene (NHC) complex [PdCl2{(CN)2IMes}(PPh3)] (2) ({(CN)2IMes}: 4,5-dicyano-1,3-dimesitylimidazol-2-ylidene) and the NHC palladacycle [PdCl(dmba){(CN)2IMes}] (3) (dmba: N,N-dimethylbenzylamine) have been synthesized by thermolysis of 4,5-dicyano-1,3-dimesityl-2-(pentafluorophenyl)imidazoline (1) in the presence of suitable palladium(II) precursors. The acyclic complex 2 was formed by ligand exchange using the mononuclear precursor [PdCl2(PPh3)2] and the palladacycle 3 was formed by cleavage of the dinuclear chloro-bridged precursor [Pd(μ-Cl)(dmba)]2. The new NHC precursor 1-benzyl-4,5-dicyano-2-(pentafluorophenyl)-3-picolylimidazoline (5) was formed by condensation of pentafluorobenzaldehyde with N-benzyl-N'-picolyldiaminomaleonitrile (4). The NHC palladacycle [PdCl2{(CN)2IBzPic}] (6) ({(CN)2IBzPic}: 1-benzyl-4,5-dicyano-3-picolylimidazol-2-ylidene) was prepared by in situ thermolysis of 5 in the presence of [PdCl2(PhCN)2]. The three palladium(II) complexes were characterized by NMR and IR spectroscopy, mass spectrometry and elemental analysis. In addition, the molecular structures of 2 and 3 were determined by X-ray diffraction. The π-acidity of (CN)2IBzPic was compared with (CN)2IMes and perviously reported π-acidic imidazol-2-ylidenes by NBO analysis. The Mizoroki-Heck (MH) reactions of various aryl halides with n-butyl acrylate were performed in the presence of complexes 2, 3 and 6. The new precatalysts showed high activity in the MH reactions giving good-to-excellent product yields with 0.1 mol-% precatalyst. The nature of the catalytically active species of 2, 3 and 6 was investigated by poisoning experiments with mercury and transmission electron microscopy. It was found that palladium nanoparticles formed from the precatalysts were involved in the catalytic process. The new precatalysts [PdCl2{(CN)2IMes}], [PdCl(dmba){(CN)2IMes}] and [PdCl2{(CN)2IBzPic}] have been prepared as candidates for the Mizoroki-Heck reaction and used in catalytic screening for reactions between n-butyl acrylate and 27 aryl bromides.

Rhodium(III)-catalyzed C-H olefination for the Synthesis of ortho-alkenyl phenols using an oxidizing directing group

By using an oxidizing directing group, a mild, efficient Rh(III) catalyzed C-H olefination reaction between N-phenoxyacetamides and alkenes was developed. This reaction provided a straightforward way for the synthesis of ortho-alkenyl phenols, and the directing group is traceless in the product.

Silanol: A traceless directing group for Pd-catalyzed o -alkenylation of phenols

A silanol-directed, Pd(II)-catalyzed C-H alkenylation of phenols is reported. This work features silanol, as a novel traceless directing group, and a directed o-C-H alkenylation of phenols. This new method allows for efficient synthesis of diverse alkenylated phenols, including an estrone derivative.