オレフィンのC-H機能化におけるコバルト・ディニトロソアルカン複合体
Jennifer M Schomaker1, W Christopher Boyd, Ian C Stewart
1Department of Chemistry, University of California, Berkeley, California 94720, USA.
Journal of the American Chemical Society
|March 6, 2008
まとめ
コバルト・ディニトロアルカン複合体はアルケンのC-H機能化を触媒する. これらの複合体は,ミカエル受容体へのアルケンの添加を可能にし,その後,触媒の再生と機能化されたアルケンの放出が続きます.
科学分野:
- 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
- オーガニック・シンセシス オーガニック・シンセシス
背景:
- C-H機能化は,有機化学における重要な変換である.
- コバルト複合体は,触媒プロセスにユニークな反応性を提供します.
研究 の 目的:
- アルケンのC-H機能化におけるコバルト・ディニトロアルカンの複合体の有用性を実証する.
- アルケンの改変のためのコバルト中間物質を含む触媒サイクルを開発する.
主な方法:
- アルケンがテトラメチルcyclopentadienylコバルトdicarbonyl (Me4CpCo(CO) 2) と酸化窒素 (NO) と反応する.
- 中間コバルトディニトロアルカンの複合物のデプロトネーション.
- マイケルの受け入れ者への追加.
- 機能化されたアルケンを放出するためのレトロサイクル添加反応.
主要な成果:
- コバルト・ディニトロアルカン複合体の形成.
- デプロトネーションが成功し,ミカエル受容体に追加されました.
- コバルト触媒の再生はレトロサイクル添加による.
- 機能化されたアルケンの放出.
結論:
- コバルト・ディニトロアルカン複合体は,アルケンのC-H機能化のための効果的な触媒である.
- 中間コバルト種を含む触媒サイクルが確立されています.
- この方法は,機能化されたアルケンのための新しい経路を提供します.
関連する概念動画
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01:16[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.
01:16Cycloaddition 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.
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
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.
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.
01:29Diels–Alder Reaction: Characteristics of Dienes
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
01:27Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
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.
01:23Properties of Organometallic Compounds
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.