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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

2.1K
Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
2.1K
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

3.4K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
3.4K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

8.6K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
8.6K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.2K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.2K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.7K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
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Site-Isolated Rhodium(II) Metalloradicals Catalyze Olefin Hydrofunctionalization.

Zihang Qiu1, Hao Deng1, Constanze N Neumann1

  • 1Department of Heterogeneous Catalysis, Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany.

Angewandte Chemie (International Ed. in English)
|February 5, 2024
PubMed
Summary

Site isolation of Rh(II) metalloradicals within a metal-organic framework (MOF) host prevents dimerization and enables thermal catalysis. This breakthrough overcomes previous limitations, paving the way for new catalytic applications.

Keywords:
MOF catalysisMOF site-isolationRh(II) metalloradicalshydrogermylation catalysishydrosilylation catalysis

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Area of Science:

  • Materials Science
  • Catalysis
  • Coordination Chemistry

Background:

  • Rhodium(II) porphyrin complexes exhibit unique radical character and small molecule activation capabilities.
  • Catalysis using Rh(II) porphyrins is hindered by facile dimerization and formation of stable Rh(III)-X intermediates, impeding catalytic turnover.
  • Site isolation strategies are crucial for stabilizing reactive metal centers in catalysis.

Purpose of the Study:

  • To overcome the catalytic limitations of Rh(II) porphyrins by preventing dimerization.
  • To enable Rh(II) metalloradicals to participate in thermal catalysis through site isolation.
  • To develop a direct MOF synthesis route for metalated porphyrin linkers.

Main Methods:

  • Direct synthesis of metal-organic frameworks (MOFs) like PCN-224 and PCN-222 using linkers with transition-metal alkyl moieties.
  • Photolysis of Rh(III)-C bonds to generate isolated Rh(II) metalloradicals within the MOF.
  • Characterization of the resulting MOFs to confirm site isolation and absence of Rh(0) nanoparticles.

Main Results:

  • Successful site isolation of Rh(II) metalloradicals within the pores of PCN-224 and PCN-222 MOFs.
  • Protection of Rh(II) metalloradicals from dimerization, a key challenge in their catalytic application.
  • Demonstration of thermal catalysis mediated by the isolated Rh(II) metalloradicals within the MOF host.

Conclusions:

  • Site isolation in MOFs is an effective strategy to stabilize reactive Rh(II) metalloradicals.
  • This approach unlocks the potential of Rh(II) porphyrins for thermal catalysis, overcoming previous limitations.
  • The developed MOF synthesis provides a versatile platform for designing advanced catalytic materials.