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関連する概念動画

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
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
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

3.1K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic...
3.1K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

6.9K
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.
6.9K
Halogenation of Alkenes02:46

Halogenation of Alkenes

17.1K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
17.1K

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関連する実験動画

Updated: May 2, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

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

Published on: November 30, 2022

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コバルトで触媒化されたC-Hボリレーション.

Jennifer V Obligacion1, Scott P Semproni, Paul J Chirik

  • 1Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.

Journal of the American Chemical Society
|March 5, 2014
PubMed
まとめ

新しいコバルト触媒は,温和な条件下でヘテロサイクルとアレンのC-Hボリレーションを効率的に実行します. これらの触媒は低負荷でも高い活性を示し,過剰なボラン反応剤を必要としません.

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:

  • 触媒性C-Hボリレーションは,有機分子の機能化に不可欠である.
  • 効率的で温和な触媒システムの開発は,依然として重要な課題です.

研究 の 目的:

  • C-Hボリレーションのための新しいピンサー・リガートコバルト複合体を合成し,評価する.
  • ヘテロサイクルとアレンのボリル化のための触媒活性と反応条件を調査する.

主な方法:

  • ピンサー・リガートコバルト複合物の合成.
  • C-Hボリレーション反応の触媒試験.
  • 反応条件の最適化 (温度,触媒の負荷,反応剤).

主要な成果:

  • 合成されたコバルト複合体は,C-Hボリレーションのための高い触媒活性を示します.
  • 反応は,過剰なボラン反応剤を必要とせずに,穏やかな条件下で進行します.
  • メチルフラン-2-カルボキシラートでは,環境温度で低触媒負荷 (0.02 mol %) で高い周回率 (最大5000) が達成されました.

結論:

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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  • ピンサーリガートコバルト複合体は,C-Hボリレーションの効果的な触媒である.
  • 触媒システムは,軽度で効率的で,低負荷のボリレーションアプローチを提供します.
  • 観察された反応性を説明するために,コバルト (I) - (III) リドックスカップルを含む触媒サイクルが提案されています.