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関連する概念動画

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.5K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.5K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.8K
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...
3.8K
Radical Formation: Addition00:47

Radical Formation: Addition

2.1K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
2.1K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.2K
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.
2.2K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.5K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.5K
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

2.1K
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.
2.1K

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関連する実験動画

Updated: Dec 17, 2025

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

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非対称なニオケタライズドラジカル・リレー・リデュークティブ・カップリング

Xiaofeng Wei1, Wei Shu1, Andrés García-Domínguez1

  • 1Department of Chemistry, University of Zurich, Winterthurerstrasse 190, Zurich, CH 8057, Switzerland.

Journal of the American Chemical Society
|June 30, 2020
PubMed
まとめ
この要約は機械生成です。

この研究では,アルケンの新しい非対称的還元性二炭素機能化が導入されました. この方法は,すぐに利用可能なハライドとオレフィンを使用して,高ステレオ選択性を有するキラルアリファティックな構造を効率的に作成します.

さらに関連する動画

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

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関連する実験動画

Last Updated: Dec 17, 2025

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

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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

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科学分野:

  • 有機化学
  • カタリシス
  • 非対称合成

背景:

  • アルケンの二酸化炭素機能化は,アリファティック化合物の合成に不可欠である.
  • この変換の触媒的非対称な変数は限られている.
  • 還元的なクロスカップリング戦略は潜在的な利点を提供します.

研究 の 目的:

  • アルケンの高効率の非対称な分子間ニッケル触媒による還元性二炭素機能化を開発する.
  • Csp2とCsp3ハリドを様々なオレフィンに同時に添加する.
  • チラルの構成要素の合成において高い地域とエナチオ選択性を達成する.

主な方法:

  • ニッケル触媒による還元性二炭水化物機能化アプローチを用いた.
  • 簡単に手に入るCsp2とCsp3ハライドを電化物として使用した.
  • 室温でのビニルアミド,ビニルボラン,ビニルフォスフォナートとの反応を調査した.
  • ステレオ制御のために,現地で生成されたキラルアルキルNi (III) -インターミディアートを活用した.

主要な成果:

  • アルケンの高度な地域およびエナチオセレクティブの二酸化炭素機能化を達成した.
  • オレフィンに2つの異なる電ophilesの同時添加を示した.
  • ステレオ定義のCsp3-Csp2結合形成のために, (l) - ((+)) - アイソレウシンキラルビソクサゾリンリガンドを成功裏に使用した.
  • アシンメトリック・ラディカル・リレー・リダクティブ・カップリング (ARRRCs) によるキラル・アミドの合成を示した.

結論:

  • アルケンの新しく効率的な非対称な分子間ニッケル触媒による還元性二炭素機能化を提示した.
  • アミンやオクサゾリンのようなキラルの構成要素を組み立てる方法の合成的有用性を強調した.
  • ステレオ制御されたCsp3-Csp2結合形成のための新しい経路を,敏感な有機金属反応剤なしで確立した.