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関連する概念動画

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

10.1K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
10.1K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

7.8K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
7.8K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

19.8K
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.
19.8K
Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids01:02

Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids

2.1K
Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.
2.1K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

2.1K
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
2.1K
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives01:35

Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

1.8K
Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.
1.8K

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Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
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Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

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デカルボキシル化ボリル化

Chao Li1, Jie Wang1, Lisa M Barton1

  • 1Department of Chemistry, The Scripps Research Institute (TSRI), La Jolla, CA 92037, USA.

Science (New York, N.Y.)
|April 15, 2017
PubMed
まとめ
この要約は機械生成です。

新しいニッケル触媒反応は 炭酸をボロ酸エステルに効率的に変換します この方法は,重要なアルキルボロン酸薬と新しい酵素阻害剤の合成を簡素化します.

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Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
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科学分野:

  • 有機化学
  • 薬剤化学
  • キャタリシス

背景:

  • アルキルボロン酸とエステルは,価値ある合成中間物質ですが,その準備は困難です.
  • これらの化合物を合成するための既存の方法は,しばしば複雑な手順または限られた範囲を伴う.

研究 の 目的:

  • 機能化されたアルキルボロナートエステルを製造するためのシンプルで実用的で広範な方法の開発.
  • 薬剤や酵素阻害剤を含む生物学的に重要な分子の合成にこの新しい方法を適用する.

主な方法:

  • カーボキシル酸誘導体をボロナートエステルに変換するためのニッケル触媒反応が開発された.
  • この反応は,アミド結合形成に類似した活性化戦略を用いる.
  • この方法はペプチド合成とα-アミノボロン酸の製造に適用された.

主要な成果:

  • この反応は,豊富な炭酸代用物から,密度が高いアルキルボロナートエステルへの迅速なアクセスを提供します.
  • アルキルボロン酸薬のVelcadeとNinlaroの合成が促進された.
  • バンコマイシンのボロン酸アナログは,高いステレオ選択性で合成されました.
  • リバーシブルな共性結合特性を持つヒト中性粒子の新種の強力な阻害剤が発見されました.

結論:

  • 開発されたニッケル触媒反応は,アルキルボロナートエステルへの多用途かつ効率的な経路を提供します.
  • この方法論は重要な医薬品の合成を大幅に簡素化し,新しい生物活性剤の発見を可能にします.
  • この方法は有機合成と薬剤開発の 幅広い応用が期待されています