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相关概念视频

Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.7K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

8.4K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
8.4K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

1.9K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
1.9K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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

3.1K
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...
3.1K
Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

5.5K
Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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帕拉介导的C ((sp

Shih-Yun Chen1, Rong Chang2, Zhong-Xin Lin1

  • 1Department of Applied Science, National Taitung University, Taitung, Taiwan 95092, R.O.C.

The Journal of organic chemistry
|June 5, 2023
PubMed
概括

这项研究引入了一种新的催化方法,通过激活C(sp3) -H键来合成替代的胺. 这种简单的方法产生了各种各样的N-{CH2-aryl/alkyl) -N-{pyridin-2-yl) 胺,具有广泛的功能组兼容性.

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科学领域:

  • 有机化学 有机化学
  • 催化剂是一种催化剂.
  • 合成方法论 合成方法论

背景情况:

  • 催化反应在现代有机合成中至关重要.
  • sp3) -H键激活提供了一个有效的途径来功能化亚利法性碳.
  • 开发复杂分子的新型合成策略仍然是一个关键的挑战.

研究的目的:

  • 开发一种简单的合成方法,用于N-CH2-aryl/alkyl) 替代的N-pyridin-2-yl) 胺.
  • 为了探索这种转换的介导的C ((sp3) -H键激活.
  • 证明合成化合物的实用性,并提出一种合成途径,以获得2-aminopyridine衍生物.

主要方法:

  • 帕拉 (II) 乙烯酸中介的C (sp3) -H键激活N-甲基-N (pyridin-2-yl) 胺.
  • 使用质谱学,NMR光谱学和X射线晶体学,形成和结构阐明双核轮中间体.
  • 密度函数理论计算和动态同位素效应实验,以提出一个反应机制.

主要成果:

  • 成功合成了一系列N-(CH2-aryl/alkyl) 替代的N-(pyridin-2-yl) 胺基.
  • 在C ((sp3) -H功能化步骤中表现出良好的功能组耐受性.
  • 关键的双核拉循环中间体的解.
  • 提出了一个可信的反应机制,得到计算和实验数据的支持.
  • 通过debenzoylation成功地将N- ((CH2-aryl) -N- ((pyridin-2-yl) -benzamides转化为N- ((CH2-aryl) -2-aminopyridines.

结论:

  • 已经建立了一种简单有效的催化方法来激活和功能化C ((sp3) -H.
  • 该方法允许合成各种N-(CH2-aryl/alkyl) 替代的N-(pyridin-2-yl) 胺,具有广泛的基质范围.
  • 开发的路线提供了获取有价值的2-aminopyridine衍生物的途径.