Jove
Visualize
お問い合わせ
JoVE
x logofacebook logolinkedin logoyoutube logo
JoVEについて
概要リーダーシップブログJoVEヘルプセンター
著者向け
出版プロセス編集委員会範囲と方針査読よくある質問投稿
図書館員向け
推薦の声購読アクセスリソース図書館諮問委員会よくある質問
研究
JoVE JournalMethods CollectionsJoVE Encyclopedia of Experimentsアーカイブ
教育
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab Manual教員リソースセンター教員サイト
利用規約
プライバシーポリシー
ポリシー

関連する概念動画

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

3.3K
The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
3.3K
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

10.4K
Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
10.4K
β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

4.0K
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.
4.0K
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

4.3K
Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
4.3K
Esters to Alcohols: Hydride Reductions01:17

Esters to Alcohols: Hydride Reductions

5.0K
Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...
5.0K
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

21.1K
The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.
21.1K

こちらも読む

関連記事

共著者、ジャーナル、引用グラフによってこの研究に関連する記事。

並び替え
Same author

Correction to "Photoactive Iminobismuthanes for Catalytic C-H Amination".

Journal of the American Chemical Society·2026
Same author

C-glycoside synthesis via radical cross-coupling of glycohydrazides.

Nature·2026
Same author

Deoxygenative Arylation of Allylic/Benzylic Esters through Cooperative Photoredox/Nickel Catalysis.

Organic letters·2026
Same author

Decarboxylative Deuteroalkylation of Olefins: A Strategy for Synthesis of Deuterium-Labeled Molecules.

The Journal of organic chemistry·2026
Same author

Stereoretentive radical-based alkyl-alkyl cross-coupling.

Science (New York, N.Y.)·2026
Same author

On the Ability of Bismuth to Couple Weakly Coordinating Anions.

Angewandte Chemie (International ed. in English)·2026

関連する実験動画

Updated: Mar 16, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

8.0K

レドックス活性エステル

Fumihiko Toriyama1, Josep Cornella1, Laurin Wimmer1

  • 1Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of the American Chemical Society
|August 23, 2016
PubMed
まとめ
この要約は機械生成です。

この研究は,有機金属反応剤による酸化還元活性エステルの新しい鉄触媒クロスカップリングを導入する. この持続可能な方法は,C−C結合形成の伝統的なニッケル触媒に優れている.

さらに関連する動画

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
07:07

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Published on: March 12, 2015

10.1K
Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
06:52

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

38.0K

関連する実験動画

Last Updated: Mar 16, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

8.0K
Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
07:07

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Published on: March 12, 2015

10.1K
Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
06:52

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

38.0K

科学分野:

  • 有機化学
  • カタリシス
  • 持続可能な化学

背景:

  • アルキルハリドを含むニッケル (Ni) と鉄 (Fe) の触媒を用いた単一の電子移転クロスカップリングに関する数十年の研究がある.
  • これらの方法は,有機合成におけるC−C結合形成に不可欠である.

研究 の 目的:

  • 酸化還元活性エステルとオルガノシンとオルガノマグネシウムの種をFe触媒を用いて初めて交配することを実証する.
  • この変換のFe触媒とNi触媒の有効性を比較する.

主な方法:

  • 最初アルキルハリドのために開発されたFeベースの触媒システムを使用した.
  • オルガノシンとオルガノマグネシウムの反応剤と結合した,孤立した,およびインシット製のリドックス活性エステル.
  • 様々な基板でNi触媒と直接比較を行った.

主要な成果:

  • 酸化還元活性エステルと,Fe触媒を用いた有機金属反応剤の交互結合が成功しました.
  • Fe触媒による新しい方法の拡張性と持続性を実証した.
  • いくつかのケースで,NiのカタリスタよりもFeのカタリスタの明らかな利点が特定されました.

結論:

  • 開発されたFe-触媒クロスカップリングは,C-C結合形成における重要な進歩を表しています.
  • この方法は,既存のNi触媒反応に対して,持続可能でスケーラブルな代替手段を提供する.
  • Fe触媒は有機合成におけるより広範な応用が期待されている.