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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
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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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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Catalytic Reductive Carbene Transfer Reactions.

Christopher Uyeda1, Annah E Kalb1

  • 1Department of Chemistry, Purdue University, West Lafayette, IN 47907, USA.

Chem Catalysis
|June 6, 2022
PubMed
Summary
This summary is machine-generated.

This study introduces a safer carbene transfer catalysis method using gem-dihaloalkanes and gem-dihaloalkenes instead of unstable diazo compounds. This approach enables cyclopropanation with non-stabilized carbenes and novel cycloadditions.

Keywords:
carbenescycloadditionstransition metal catalysis

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Catalytic carbene transfer reactions traditionally use diazo precursors.
  • Diazoalkanes pose safety risks due to exothermic decomposition, limiting their synthetic utility.
  • Existing methods primarily employ stabilized diazoacetates.

Purpose of the Study:

  • To present an alternative carbene transfer catalysis strategy.
  • To utilize stable gem-dihaloalkanes and gem-dihaloalkenes as carbene precursors.
  • To expand the scope of carbene transfer reactions, including non-stabilized carbenes.

Main Methods:

  • Generation of metal carbenoids from gem-dihaloalkanes and gem-dihaloalkenes.
  • Application of these carbenoids in catalytic carbene transfer reactions.
  • Exploration of cyclopropanation and cycloaddition reactions.

Main Results:

  • Demonstrated the feasibility of using gem-dihaloalkanes/alkenes as stable carbene precursors.
  • Achieved cyclopropanation reactions with non-stabilized carbenes (methylene, isopropylidene, vinylidene).
  • Enabled novel cycloaddition reactions, including [4 + 1]-cycloadditions, via distinct mechanistic pathways.

Conclusions:

  • Gem-dihaloalkanes and gem-dihaloalkenes offer a safer and versatile alternative to diazo compounds for carbene transfer.
  • This methodology broadens the accessibility of carbene transfer catalysis to a wider range of substrates and reaction types.
  • The distinct mechanisms allow for the development of new synthetic transformations.