Highly regio- and stereoselective hydrophosphinylation of acetylenes with diphenylphosphine oxide catalyzed by immobilization of rhodium in MCM-41

Heterogeneous C-S coupling reaction of thiols with polychloroalkanes or alkyl halides was achieved at 30 or 80°C in the presence of 5 mol% of an MCM-41-immobilized bidentate phosphine rhodium complex (MCM-41-2P-RhCl(PPh 3 )) and triethylamine, yielding a variety of formaldehyde dithioacetals, ethylenedithioethers and unsymmetric thioethers in good to excellent yields. This heterogeneous rhodium catalyst can be easily recovered and recycled by simple filtration of the reaction solution and used for at least 10 consecutive trials without significant loss of activity.

“…[20] The P:Rh mole ratio of the MCM-41-2P-RhCl(PPh 3 ) was determined to be 4.5 from elemental analyses.…”

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

A highly efficient heterogeneous rhodium(I)‐catalyzed C–S coupling reaction of thiols with polychloroalkanes or alkyl halides under mild conditions

Xia

Yao

Cai

2015

“…Large specific surface area of MCM‐41 that possesses a lot of silanol groups leads to simple modification of its surface by other functional groups . Also high specific pore volume (up to 1.3 ml/g) of MCM‐41 allows anchoring of huge molecules such as organic ligands and metal complexes into hexagonal channels . Furthermore, high thermal stability of this nanostructural compound allows doing organic reaction in high temperatures .…”

Section: Introductionmentioning

confidence: 99%

Pd‐SBT@MCM‐41: As an efficient, stable and recyclable organometallic catalyst for C‐C coupling reactions and synthesis of 5‐substituted tetrazoles

Nikoorazm

Ghorbani‐Choghamarani

Ghobadi

et al. 2017

A palladium S-benzylisothiourea complex was anchored on functionalized MCM-41 (Pd-SBT@MCM-41) and applied as efficient and reusable catalyst for the synthesis of 5-substituted 1H-tetrazoles using [2 + 3] cycloaddition reaction of various organic nitriles with sodium azide (NaN 3 ) in poly(ethylene glycol) (PEG) as green solvent. Also this catalyst was applied as an versatile organometallic catalyst for Suzuki cross-coupling reaction of aryl halides and phenylboronic acid (PhB(OH) 2 ) or sodium tetraphenyl borate (NaB(Ph) 4 ). This nanocatalyst was characterized by thermal gravimetric analysis (TGA), X-ray Diffraction (XRD), scanning electron microscopy (SEM), inductively Coupled Plasma (ICP) and N 2 adsorption-desorption isotherms techniques. Recovery of the catalyst is easily achieved by centrifugation for several consecutive runs.

“…Wilkinson's catalyst, i.e. tris(triphenylphosphine)rhodium(I) chloride, RhCl(PPh 3 ) 3 , is one of the most used homogeneous catalysts with marked activity and selectivity in organic reactions . This catalyst has been supported on a variety of inorganic solids, but little attention has been paid to the heterogenization of the Wilkinson's catalyst on magnetic materials.…”

Section: Introductionmentioning

confidence: 99%

Magnetically water‐dispersible and recoverable rhodium organometallic catalyst derived from Wilkinson's catalyst for promoting organic reactions

Nejat

Mahjoub

2016

A novel magnetic rhodium catalyst was prepared through immobilizing Wilkinson's catalyst on the surface of silica-coated iron oxide nanoparticles. After (thio)diphenylphosphine (─S&─PPh 2 ) was modified on the surface of the silicacoated iron oxide nanoparticles, tris(triphenylphosphine)rhodium(I) chloride was employed to synthesize the Rh(Cl)(PPh 3 ) 2 (Ph 2 P&─S&─) complex, affording a rhodium loading of 0.16 mmol g −1. The Rh(I) organometallic magnetic nanoparticles form a novel class of heterogeneous catalyst which is particularly suitable for the practice of organic synthesis. The prepared system exhibits high catalytic efficiency in Suzuki-Miyaura and Miyaura-Michael reactions in ethanol-water solution. High yield, low reaction times, use of green solvents and non-toxicity of the catalyst are the main merits of this protocol. Also, magnetic separation is an environmentally friendly alternative for the recovery of the catalyst, since it minimizes energy and catalyst loss by preventing mass loss and oxidation. The produced catalyst was characterized using a variety of techniques.