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関連する概念動画

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

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.4K
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.
9.4K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

14.8K
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...
14.8K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

4.0K
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...
4.0K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

4.3K
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
4.3K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

21.8K
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.
21.8K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

4.7K
Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
4.7K

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Updated: Mar 25, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

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制御可能な移転水素化による触媒的可逆アルケネ-ニトリル相互変換

Xianjie Fang1, Peng Yu1, Bill Morandi2

  • 1Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Nordrhein-Westfalen 45470, Germany.

Science (New York, N.Y.)
|February 26, 2016
PubMed
まとめ

研究者は,ニトリルを用いたアルケンのより安全な水素化反応を開発した. この方法は有毒な水素シアン化物 (HCN) を避け,価値ある化学物質のための新しい合成経路を提供します.

科学分野:

  • 有機化学
  • カタリシス
  • 合成方法論

背景:

  • ナトリルとアルケンは,材料,医薬品,農薬の合成において重要な構成要素です.
  • 伝統的な水素化法では,しばしば有毒な水素シアン化物 (HCN) に依存し,重大な安全リスクが生じます.
  • より安全で多用途な合成経路の開発は,現代の化学研究にとって不可欠です.

研究 の 目的:

  • アルキルニトリルとアルケンの間の新しいニッケル触媒移転水酸化反応を報告する.
  • 伝統的なHCNベースの水酸化方法のより安全な代替手段を提供するためです.
  • リトロヒドロシアネーションとアンチ・マルコヴニコフ・リージオセレクティビティを含む新しい合成の可能性を探求する.

主な方法:

  • 転移ヒドロシアネーション反応を媒介するためにニッケル触媒を使用した.
  • 基板の適用範囲を示すために,幅広いアルキルニトリルとアルケーン (60例) を使用した.
  • リバーシブルアルケンの水機能化のための熱力学的に制御された転送反応を調査した.

主要な成果:

  • 様々なアルキルニトリルとアルケンのニッケル触媒による転移水酸化を成功裏に実証した.
  • 水素化過程で反マルコフニコフ領域選択性を達成した.

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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関連する実験動画

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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  • 危険な反応剤を回避する 逆戻り可能な水素機能化の可能性を示した
  • 結論:

    • 開発されたニッケル触媒による移転水酸化は,従来の方法よりも安全で効率的な代替手段を提供します.
    • この戦略は,有機合成におけるニトリルとアルケンの合成有用性を拡大する.
    • この研究は,持続可能で制御可能な水素機能化反応の開発において重要な進歩を示しています.