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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.
Heterogeneous Catalysis01:22

Heterogeneous Catalysis

Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.

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関連する実験動画

Updated: May 8, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)

Published on: January 17, 2020

サイト選択性の予測モデルを備えた,触媒制御のアリファティックC-H酸化.

Paul E Gormisky1, M Christina White

  • 1Department of Chemistry, University of Illinois Urbana-Champaign , Urbana, Illinois 61801, United States.

Journal of the American Chemical Society
|September 12, 2013
PubMed
まとめ

この研究は,選択的アリファティックC-H結合酸化のための新しい非ヘム鉄触媒を導入しています. 触媒は,多様な有機分子におけるサイト選択性に対する予測可能な制御を示し,幅広い合成アプリケーションを提供しています.

科学分野:

  • 有機化学 オーガニック・ケミストリー
  • カタリシス カタリシス カタリシス
  • 合成方法論 合成方法論

背景:

  • アリファティックC-H結合は有機分子に至る所に存在し,その選択的酸化が合成における重要な課題となっている.
  • 既存の触媒は,多くの場合,広範な基板範囲や酸化部位選択性に対する予測可能な制御が欠けている.
  • 酵素のような,予測可能な反応性に対する制御は,合成アプリケーションでは非常に望ましい.

研究 の 目的:

  • 選択的アリファティックC-H結合酸化のための単純な小分子触媒を開発する.
  • 幅広い基板で予測可能な触媒制御サイト選択性を達成するために.
  • 基板の性質と触媒制御された選択性を相関させるモデルを確立する.

主な方法:

  • 非ヘム鉄の触媒の開発.
  • トポロジ的に多様なアリファティック基板で触媒の性能をテストする.
  • 基板の物理的性質と観測された部位選択性を相関させる定量分析.

主要な成果:

  • 単純な非ヘム鉄触媒が成功して合成され,特徴づけられました.
  • 触媒は,様々なアリファティックC−H結合の酸化において予測可能なサイト選択性を示した.

さらに関連する動画

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

関連する実験動画

Last Updated: May 8, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)

Published on: January 17, 2020

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
12:08

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

  • さまざまな基板に対して,調理性産量が得られました.
  • 基板の性質に基づいて選択性を予測するための定量モデルが確立されました.

    • 結論:

    • 開発された非ヘム鉄触媒は,選択的アリファティックC-H結合酸化のための強力なツールを提供します.
    • サイト選択性における触媒制御の予測性が達成され,固有の基板偏好を克服しました.
    • この研究は,C-H活性化の分野を発展させ,将来の触媒の設計のための基礎を提供します.