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The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...
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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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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.
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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.
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Process Development of Heterogeneous Rh Catalyzed Carbene Transfer Reactions Under Continuous Flow Conditions.

Tahani A C A Bayrakdar1, Camille Lescot1

  • 1Chimie ParisTech PSL, CNRS 8060, Institute of Chemistry for Life and Health Sciences (i-CLeHS), 11, rue Pierre et Marie Curie, 75005, Paris, France.

Chemsuschem
|May 15, 2023
PubMed
Summary
This summary is machine-generated.

A novel Rh-based catalyst enables efficient carbene transfer reactions under continuous flow conditions. This heterogeneous catalyst demonstrates excellent recyclability and allows for sequential transformations, producing diverse compound families.

Keywords:
carbene transformationscatalysiscontinuous processflow chemistryrhodium

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Area of Science:

  • Catalysis
  • Organic Chemistry
  • Chemical Engineering

Background:

  • Heterogeneous catalysis offers advantages in separation and recycling.
  • Continuous flow chemistry enables efficient and scalable reactions.
  • Carbene transfer reactions are fundamental in organic synthesis.

Purpose of the Study:

  • To develop a simple Rh-based heterogeneous catalyst for carbene transfer reactions.
  • To investigate catalyst immobilization methods in a column reactor.
  • To evaluate the catalyst's performance in terms of activity, recyclability, and sequential transformations.

Main Methods:

  • Immobilization of a Rh-based catalyst in a column reactor using two distinct methods.
  • Functionalization of various X-H bonds (X=O, S, Si, CH2) via carbene insertion.
  • Performance evaluation under mild, continuous flow conditions.

Main Results:

  • Successful carbene transfer and cyclopropenation reactions with diverse substrates.
  • Achieved up to 5 catalytic cycles for O-H insertion reactions with catalyst recycling.
  • Demonstrated 10 consecutive runs for sequential substrate transformations without loss of activity.

Conclusions:

  • The developed Rh-based heterogeneous catalyst is highly effective for carbene transfer reactions.
  • Continuous flow operation and catalyst immobilization facilitate efficient and sustainable synthesis.
  • The catalyst's robustness enables the production of diverse compound libraries through sequential reactions.