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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.0K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.0K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.1K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.1K
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

9.2K
Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
When dissolved in liquid ammonia, an alkali metal,...
9.2K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.1K
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...
2.1K
Photoluminescence: Applications01:14

Photoluminescence: Applications

386
Photoluminescence offers a wide range of applications due to its inherent sensitivity and selectivity. This technique allows for both direct and indirect analyses of the analyte. Direct quantitative analysis is possible when the analyte exhibits a favorable quantum yield for fluorescence or phosphorescence. However, an indirect analysis may be feasible if the analyte is not fluorescent or phosphorescent, or if the quantum yield is unfavorable. Indirect methods include reacting the analyte with...
386
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.3K
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...
3.3K

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関連する実験動画

Updated: Jun 20, 2025

Preparation and Use of Samarium Diiodide SmI2 in Organic Synthesis: The Mechanistic Role of HMPA and NiII Salts in the Samarium Barbier Reaction
12:22

Preparation and Use of Samarium Diiodide SmI2 in Organic Synthesis: The Mechanistic Role of HMPA and NiII Salts in the Samarium Barbier Reaction

Published on: February 4, 2013

33.0K

可視光アンテナリガンド活性化されたサマリウム触媒による還元変換

Takahito Kuribara1,2, Ayahito Kaneki2, Yu Matsuda2

  • 1Institute for Advanced Academic Research, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.

Journal of the American Chemical Society
|July 20, 2024
PubMed
まとめ

この研究は,効率的な還元変換のための可視光アンテナリガンドを持つ新しいサマリウム (Sm) 触媒を導入する. 触媒は,ピナコール結合およびその他の単電子還元反応のための穏やかな条件を可能にします.

さらに関連する動画

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

17.1K
Identification of Small Molecule-binding Proteins in a Native Cellular Environment by Live-cell Photoaffinity Labeling
10:49

Identification of Small Molecule-binding Proteins in a Native Cellular Environment by Live-cell Photoaffinity Labeling

Published on: September 20, 2016

12.6K

関連する実験動画

Last Updated: Jun 20, 2025

Preparation and Use of Samarium Diiodide SmI2 in Organic Synthesis: The Mechanistic Role of HMPA and NiII Salts in the Samarium Barbier Reaction
12:22

Preparation and Use of Samarium Diiodide SmI2 in Organic Synthesis: The Mechanistic Role of HMPA and NiII Salts in the Samarium Barbier Reaction

Published on: February 4, 2013

33.0K
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

17.1K
Identification of Small Molecule-binding Proteins in a Native Cellular Environment by Live-cell Photoaffinity Labeling
10:49

Identification of Small Molecule-binding Proteins in a Native Cellular Environment by Live-cell Photoaffinity Labeling

Published on: September 20, 2016

12.6K

科学分野:

  • 有機化学
  • カタリシス
  • 写真化学

背景:

  • 二重サマリウム (Sm) 反応剤は,還元変換における単電子移転に不可欠である.
  • Smの反応剤の触媒的応用は,安定性や反応性の問題によりしばしば困難である.
  • 軽度で効率的な Sm-触媒反応の開発は,現在進行中の研究分野である.

研究 の 目的:

  • サマリウム触媒による還元反応のための新しいリガンドを設計する.
  • 可視光照射を用いて軽い反応条件を達成する.
  • サマリウム触媒による単電子還元変換の範囲を拡大する.

主な方法:

  • 9,10-ディフェニラントラセンの可視光アンテナを搭載した二酸化フォスフィンリガンドの設計.
  • アリルケトンとアルデヒドのサマリウム触媒によるピナコール結合の開発
  • オーガニック・アミン (DIPEA) を減量剤として使用する.
  • 反応のメカニズムをメカニズム研究で調べる.

主要な成果:

  • 温和な条件下でピナコール結合のための触媒システムの成功開発
  • 可視光照射によるSm(III) をSm(II) に還元するリガンドの役割の実証.
  • クロスピナコール結合,アザピナコール結合,フラボン二酸化,C-O結合の分裂,サイクロプロパンのC-リング開き,ケチル-オレフィン結合,ケチルとα-アミノラジカルのクロスカップリングを含む様々な単電子還元変換への触媒システムの拡張.

結論:

  • 新しい可視光アンテナリガンドは,穏やかな条件下で効率的なサマリウム触媒による還元変換を可能にします.
  • 開発された触媒システムは,有機合成におけるサマリウムの適用性を拡大する.
  • このアプローチは,サマリウム媒介の単一電子移転反応で光を活用するための新しい戦略を提供します.