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Related Concept Videos

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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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: 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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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

8.2K
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.
8.2K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

12.6K
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.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
12.6K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

19.0K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
19.0K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.7K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Solventless Catalytic C-H and C-X Functionalization without Ball Milling.

Carolina Méndez-Gálvez1, Fredrik Barnå1, Boris Olsthoorn1

  • 1Department of Chemistry - BMC, Uppsala University, P.O. Box 576, Uppsala 75123, Sweden.

The Journal of Organic Chemistry
|June 19, 2025
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Summary

This study introduces a simple, low-cost method for various metal-catalyzed chemical reactions using grinding and heating. This technique efficiently synthesizes complex molecules and modifies bioactive compounds.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Metal-catalyzed cross-coupling reactions are vital in organic synthesis.
  • Solvent-intensive methods often pose environmental and cost challenges.
  • Developing solventless catalytic protocols is a key goal in sustainable chemistry.

Purpose of the Study:

  • To present a low-cost, operationally simple, and solventless method for diverse C-H and C-X functionalizations.
  • To demonstrate the synthesis of challenging rhodacyclic complexes.
  • To enable the late-stage modification of bioactive molecules.

Main Methods:

  • Utilizing open-air grinding and heating for solventless reactions.
  • Employing rhodium (Rh), ruthenium (Ru), iridium (Ir), and palladium (Pd) catalysts.
  • Investigating eight distinct catalytic transformations.

Main Results:

  • Achieved reproducible and competitive yields for multiple catalytic reactions.
  • Successfully synthesized difficult-to-prepare rhodacyclic complexes.
  • Demonstrated the applicability to late-stage functionalization of bioactive compounds.

Conclusions:

  • The presented solventless grinding method offers a practical and efficient alternative to existing protocols.
  • This approach facilitates sustainable synthesis and modification of complex organic molecules.
  • The method is versatile and applicable to a range of metal-catalyzed reactions and substrates.