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相关概念视频

Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

10.2K
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.
10.2K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.7K
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.
7.7K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.1K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.1K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

3.8K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
3.8K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

15.8K
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
15.8K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.0K

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相关实验视频

Updated: Jul 8, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

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一种高效和化学选择性的方法来产生arynes.

Bryan E Metze1, Riley A Roberts1, Aleksandra Nilova1

  • 1Department of Chemistry, Portland State University Portland OR 97201 USA dstuart@pdx.edu.

Chemical science
|December 11, 2023
PubMed
概括

这项研究引入了一种温和而高效的方法,用于使用酸和酸产生酸. 这种方法证明了广泛的功能组兼容性,克服了以前的基生成技术的局限性.

科学领域:

  • 有机化学 有机化学
  • 合成方法论 合成方法论
  • 反应性中间体的反应性中间体

背景情况:

  • 阿林是有机合成中的多功能反应中间体.
  • 之前的基生成方法的功能组兼容性不佳,限制了它们的应用.
  • 开发温和高效的基生成协议对于扩大它们的合成实用性至关重要.

研究的目的:

  • 开发一种新的,温和和高效的方法来产生.
  • 调查开发的基生成方法的功能组兼容性.
  • 量化比较不同基生成策略的功能组耐受性.

主要方法:

  • 通过去质子化和消除"",使用盐 (TMP = 2,4,6-trimethoxyphenyl) 消除基.
  • 使用酸作为温和的基础.
  • 与各种类动物和敏感功能组 (路易斯酸,布伦斯特德酸,电性动物) 的兼容性研究.
  • 对不同基生成方法的功能组兼容性的定量分析.

主要成果:

  • 建立了一种温和,高效和广泛的基生成方法.
  • 开发的方法证明了与广泛的类动物的兼容性.
  • 该研究提出了第一个量化分析,比较跨多种基生成技术的功能组兼容性.

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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  • 敏感的功能组,包括易斯酸,布伦斯特德酸和电友,被发现与新方法兼容.
  • 结论:

    • 酸 (TMP) 盐为轻度和高效的酸生成提供了卓越的前体.
    • 开发的方法通过适应敏感的功能组,显著扩大了基化学的范围.
    • 这项工作克服了阿里因合成的关键局限性,为在有机合成中更广泛采用铺平了道路.