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関連する概念動画

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic rearrangements are...

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関連する実験動画

Updated: May 7, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

効率的なクロム (((II) 触媒による,Csp2の中心間のクロスカップリング反応.

Andreas K Steib1, Olesya M Kuzmina, Sarah Fernandez

  • 1Department of Chemistry, Ludwig-Maximilians-Universität , Butenandtstrasse 5-13, 81377 Munich, Germany.

Journal of the American Chemical Society
|September 24, 2013
PubMed
まとめ

低毒性クロミウム (II) クロライドは,室温でのクロスカップリング反応を効率的に触媒化する. この方法は,他の金属触媒と比較して,副作用が大幅に減少したよりグリーンな代替案を提供します.

さらに関連する動画

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

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

関連する実験動画

Last Updated: May 7, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

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

科学分野:

  • 有機化学 オーガニック・ケミストリー
  • 有機金属化学 有機金属化学
  • カタリシス カタリシス カタリシス

背景:

  • クロスカップリング反応は,有機合成における炭素-炭素結合の形成に不可欠である.
  • 伝統的なクロスカップリングは,しばしば有毒または高価な金属を使用し,副作用が収穫量に影響を及ぼします.
  • 効率的で選択的な触媒の開発は,合成化学の主要な課題です.

研究 の 目的:

  • 交互結合反応における低毒性クロミウム (II) クロリドの触媒活性を調査する.
  • この触媒システムの範囲を様々な有機基質で探求する.
  • クロミウム触媒結合の効率と選択性を他の移行金属と比較するために.

主な方法:

  • クロミウム (II) クロライドを,クロスカップリング反応の触媒として利用する.
  • (ヘテロ) アリルマグネシウム反応剤をN-ヘテロサイクリックハリド,アロマティックハロゲン化ケトン/イミン,アルケニルヨウ酸化物を使用する.
  • 25°Cで反応を行い,製品の産量と副産物の形成を分析する.

主要な成果:

  • クロミウム ((II) クロライドは,室温で数分以内に結合反応を効果的に触媒化しました.
  • 触媒は,多様な (ヘテロ) アリルマグネシウム反応剤を様々な電極性物質と結合し,幅広い基板範囲を示した.
  • 鉄,コバルト,またはマンガンの触媒と比較して,ホモ結合の副産物の量が著しく低いことが観察されました.

結論:

  • 低毒性クロミウム (II) クロライドは,様々なクロスカップリング反応の非常に効果的な触媒です.
  • この方法は,既存のトランジション金属触媒結合器に対して,より選択的で,潜在的にグリーンな代替手段を提供します.
  • 減少したホモカップリングにより,合成効率と原子経済性が向上します.