Jove
Visualize
お問い合わせ
JoVE
x logofacebook logolinkedin logoyoutube logo
JoVEについて
概要リーダーシップブログJoVEヘルプセンター
著者向け
出版プロセス編集委員会範囲と方針査読よくある質問投稿
図書館員向け
推薦の声購読アクセスリソース図書館諮問委員会よくある質問
研究
JoVE JournalMethods CollectionsJoVE Encyclopedia of Experimentsアーカイブ
教育
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab Manual教員リソースセンター教員サイト
利用規約
プライバシーポリシー
ポリシー

関連する概念動画

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

1.3K
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
1.3K
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

1.8K
Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
1.8K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

1.4K
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.
1.4K
Oxymercuration-Reduction of Alkenes02:36

Oxymercuration-Reduction of Alkenes

8.2K
Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
8.2K
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

1.3K
The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
1.3K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

12.4K
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...
12.4K

こちらも読む

関連記事

共著者、ジャーナル、引用グラフによってこの研究に関連する記事。

並び替え
Same author

C-glycoside synthesis via radical cross-coupling of glycohydrazides.

Nature·2026
Same author

Stereoretentive radical-based alkyl-alkyl cross-coupling.

Science (New York, N.Y.)·2026
Same author

Electronegatively substituted adamantyl units accelerate chemiexcitation of 1,2-dioxetane luminophores while preserving chemical stability.

Chemical science·2026
Same author

Enabling Access to sp<sup>3</sup>-Enriched Targeted Protein Degraders via Redox-Neutral Radical Cross-Coupling.

Angewandte Chemie (International ed. in English)·2026
Same author

Arylhydrazines: Convenient Homogeneous Reductants for Scalable Cross-Coupling.

Angewandte Chemie (International ed. in English)·2026
Same author

Decoding the Nested, Multicycle Mechanism of Ni-Catalyzed Redox-Neutral Cross-Coupling through Temperature Scanning Reaction Calorimetry.

Journal of the American Chemical Society·2025
Same journal

A Ni-Mediated Cross-Coupling Approach to Deuterated <sup>18</sup>F- Fluoromethylated (Hetero)arenes.

Journal of the American Chemical Society·2026
Same journal

Efficient Light-Driven CO<sub>2</sub> Capture and Reversible Release Enabled by Metastable Photoacid-Decorated Metal-Organic Frameworks.

Journal of the American Chemical Society·2026
Same journal

In Situ Raman Spectroscopy Reveals the Dynamic Evolution and Ethanol Dependence of SEI Structure in Li-Mediated N<sub>2</sub> Reduction Reaction.

Journal of the American Chemical Society·2026
Same journal

Solvent Esterification and Stoichiometric Control in Ambient-Grown FAPbI<sub>3</sub> Single-Crystal Solar Cells.

Journal of the American Chemical Society·2026
Same journal

Unlocking Azulene Functionalization via Strain-Induced Azulyne Intermediates.

Journal of the American Chemical Society·2026
Same journal

An Oxazine-Locked Covalent Organic Framework by a Tandem Pinner/Schiff Base Reaction for Hydrogen Peroxide Photosynthesis.

Journal of the American Chemical Society·2026
関連記事をすべて見る

関連する実験動画

Updated: May 4, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

12.3K

実践的で触媒的な還元性オレフィンカップリングです.

Julian C Lo1, Yuki Yabe, Phil S Baran

  • 1Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of the American Chemical Society
|January 17, 2014
PubMed
まとめ
この要約は機械生成です。

研究者らは,オレフィンと直接結合するための費用対効果の高い鉄触媒法を開発した. この反応は,阻害されたバイサイクルシステムや四次中心を含む複雑な分子を効率的に生成し,新しい合成経路を提供します.

さらに関連する動画

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

6.6K
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.5K

関連する実験動画

Last Updated: May 4, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

12.3K
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

6.6K
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.5K

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:

  • オレフィン直接結合は,有機合成における重要な変換である.
  • 既存の方法は,しばしば高価な触媒や厳しい条件を必要とする.
  • 周辺四次中心のような複雑な構造物へのアクセスは,依然として困難です.

研究 の 目的:

  • オレフィン直接結合のためのリドックス経済的で費用対効果の高い方法を開発する.
  • 容易に入手可能な起始材料を使用して,挑戦的な分子構造の合成を可能にします.
  • 複雑な有機化合物の頑丈でスケーラブルな合成経路を提供する.

主な方法:

  • オレフィンの直接結合のために,安価な鉄触媒を使用した.
  • 酸化還元プロセスを促進するために,シラン還元剤を使用した.
  • 分子内および分子間結合反応の両方を調査しました.

主要な成果:

  • 活性化されていないオレフィンと電子欠乏性オレフィンとの結合が成功しました.
  • 妨害されたバイサイクルのシステム,近隣の四次中心,およびサイクロプロパンが良好な収穫で生成されました.
  • 酸素と水分に対する強度が実証され,グラムスケールの合成に成功しています.

結論:

  • 報告された鉄触媒メソッドは,直接オレフィン結合の新鮮で効率的なアプローチを提供します.
  • この戦略は,以前に合成が困難だった貴重な化合物へのアクセスを提供します.
  • この反応の実用性とスケーラビリティは,合成有機化学における重要な進歩である.