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Related Concept Videos

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

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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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

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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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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

12.1K
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...
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Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

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Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Atomically precise ultrasmall copper cluster for room-temperature highly regioselective dehydrogenative coupling.

Teng Jia1, Yi-Xin Li1, Xiao-Hong Ma1

  • 1Henan Key Laboratory of Crystalline Molecular Functional Materials, Henan International Joint Laboratory of Tumor Theranostcal Cluster Materials, Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou, P. R. China.

Nature Communications
|October 29, 2023
PubMed
Summary

A novel copper cluster catalyst, Cu3NC(NHC), enables efficient, all-in-one dehydrogenative coupling reactions for C-N and C-C bond formation. This breakthrough offers enhanced activity and stability for complex chemical synthesis.

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Area of Science:

  • Catalysis
  • Organometallic Chemistry
  • Synthetic Chemistry

Background:

  • Three-component dehydrogenative coupling reactions are vital for C-N and C-C bond synthesis.
  • Developing a single catalytic system for highly efficient, all-in-one dehydrogenative coupling remains a significant challenge.

Purpose of the Study:

  • To design and synthesize a novel copper cluster catalyst with enhanced activity and stability.
  • To apply the catalyst in highly all-in-one dehydrogenative coupling transformations.
  • To elucidate the mechanistic basis for the catalyst's improved performance.

Main Methods:

  • Synthesis of a rigid-flexible-coupled copper cluster, Cu3NC(NHC), using a tridentate N-heterocyclic carbene ligand.
  • Application of the catalyst in three-component dehydrogenative coupling reactions.
  • Mechanistic investigations including density functional theory (DFT) calculations.

Main Results:

  • The Cu3NC(NHC) catalyst demonstrated high efficiency in all-in-one dehydrogenative coupling reactions.
  • The catalyst exhibited improved activity and stability due to its unique rigid-flexible structure.
  • Mechanistic studies revealed that enhanced regioselectivity arises from favorable ion pair energies and low transition states.

Conclusions:

  • The developed Cu3NC(NHC) catalyst effectively catalyzes challenging dehydrogenative coupling reactions.
  • N-heterocyclic carbene ligands play a crucial role in modifying copper clusters for enhanced catalysis.
  • This work provides a new design strategy for protecting catalytic centers and improving cluster-based catalysis.