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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.6K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.6K
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

4.8K
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
4.8K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.5K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
4.5K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

12.4K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
12.4K
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

8.7K
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
8.7K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

21.6K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
21.6K
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  2. カルバゾールとアルキルブロミドの交互結合のメカニズム的研究
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  2. カルバゾールとアルキルブロミドの交互結合のメカニズム的研究

関連する実験動画

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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カルバゾールとアルキルブロミドの交互結合のメカニズム的研究

Jun Myun Ahn1, Tanvi S Ratani1, Kareem I Hannoun1

  • 1Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.

Journal of the American Chemical Society
|August 18, 2017

PubMed で要約を見る

まとめ
この要約は機械生成です。

光活性化銅触媒は,カルバゾールとアルキルブロミドの効率的な結合を可能にします. この研究は,刺激された核愛素と銅 (II) の中介物質を含む支配的根幹経路を新型結合構築に示しています.

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

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科学分野:

  • 有機化学
  • 写真化学
  • カタリシス

背景:

  • 最近の進歩は,光を用いた温和な条件下で,有機ハライドと様々な核素の銅触媒結合を示している.
  • 新しい合成方法の開発には 反応メカニズムを理解することが重要です

研究 の 目的:

  • カルバゾールとアルキルブロミドの光誘導による銅触媒結合を調査する.
  • この反応に関与するメカニズム的経路を解明する.

主な方法:

  • EPR,NMR,トランジント吸収,UV-VISスペクトロスコーピー,ESI-MS,X線結晶学,DFT計算を含む包括的な一連のテクニックを使用しました.
  • 反応性,ステレオ化学,および製品研究を実施した.

主要な成果:

  • 銅 ((I) カーバゾリドとリチウムカーバゾリドの興奮状態がアルキルブロミドの光還元剤として作用する経路を特定した.
  • 主な経路は,カルバジルとアルキル基を生成するリチウムカルバゾリドの興奮状態を含む.
  • 銅の触媒は,鍵となる中間物質である[CuI(carb) 2-と[CuII(carb) 3-を介して進行する.
  • [CuII(carb) 3]-は持続的な基として作用し,主たるクロスカップリングを促進する.

結論:

  • この研究は,銅 (II) 複合体の多用途性を強調しています.
  • メカニズムの洞察は,光誘導の根性交互結合による新しい結合構築戦略の開発を容易にする.