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関連する概念動画

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.4K
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.
2.4K
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

2.3K
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.
2.3K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.2K
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.
9.2K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

12.8K
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.
12.8K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.9K
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...
3.9K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

10.7K
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...
10.7K

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関連する実験動画

Updated: Mar 1, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

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ピンサー・リガド・イリジウム複合体による触媒脱水C-C結合

Miles Wilklow-Marnell1, Bo Li2, Tian Zhou2

  • 1Department of Chemistry, University of Rochester , Rochester, New York 14627, United States.

Journal of the American Chemical Society
|June 9, 2017
PubMed
まとめ

ピンサー・イリジウム触媒は,ビニルアレンを脱水結合させ,ダイアリルブタディエンを形成する. この反応は,不均衡化または水素受容体によって進行し,最大90%の産物を得ることができます.

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

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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関連する実験動画

Last Updated: Mar 1, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

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

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

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科学分野:

  • 有機金属化学
  • カタリシス
  • 有機合成

背景:

  • ビニルアレーンは有機合成における多用途な構成要素である.
  • C-H機能化のための効率的な触媒方法は非常に求められています.

研究 の 目的:

  • ビニルアレンの脱水結合におけるピンサー-イリジウム複合体の触媒的活性を調べる.
  • 反応メカニズムを明らかにし,基板の範囲を調査する.

主な方法:

  • イリジウム断片 (iPrPCP) を用いた触媒
  • 密度関数理論 (DFT) の計算
  • メタロインデンの中間物質の合成と特徴付け
  • 置換されたスタイレンとの反応

主要な成果:

  • 脱水結合による (E,E) -1,4-ダイアリル-1,3-ブタジエンの形成が優勢である.
  • 不均衡化や犠牲用水素受容器によって最大90%の収量が得られる.
  • このメカニズムは,二重C−H添加により,イリジウム (III) メタロインデンの中間物質を形成する.
  • 2,4,6-トリメチルスタイレンを用いたC ((sp2) -HとC ((sp3) -H結合の証明

結論:

  • ピンサー-イリジウム複合体は,ビニルアレン脱水結合の効果的な触媒である.
  • 反応はメタロインデンの中間体を通過する.
  • 触媒システムは多用途で,様々なC−H結合を組み合わせることができます.