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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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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.
7.8K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

9.8K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
9.8K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

2.3K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.3K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
3.4K
Radical Halogenation: Thermodynamics01:34

Radical Halogenation: Thermodynamics

3.7K
The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy...
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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FON:通过水电化类型反应性的创新化组.

Sanaz Rajabalinia1, Hedieh Lotfian1, Sabrina Hoford1

  • 1Department of Chemistry, Brock University, St. Catharines, Ontario L2S 3A1, Canada.

Organic letters
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概括

一种新的方法有效地合成了化功能组,造FON,使用无金属反应. 这一策略可以实现多种应用,包括格拉姆尺度合成和用于药物化学的合物.

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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科学领域:

  • 有机化学 有机化学
  • 化学 的化学
  • 药用化学 医学化学

背景情况:

  • 新型化功能组的开发对于药物发现至关重要.
  • O-difluoroalkylhydroxylamines (FON) 是一种独特的结构图案,具有潜在的药物应用.
  • 现有的这种化合物的合成途径通常在范围或效率上是有限的.

研究的目的:

  • 报告一种新型O-difluoroalkylhydroxylamine (FON) 功能组的高效,单步合成.
  • 探索开发的合成方法的范围和局限性.
  • 为反应及其在催化中的潜在应用提供机械洞察力.

主要方法:

  • 没有金属的电化类型的添加反应.
  • 化学和区域选择性合成.
  • 多种基质范围评估.
  • 格拉姆尺度合成和地点选择性结合.

主要成果:

  • 为FON集团实现了一种新的,高效的单步合成.
  • 反应表明了广泛的基质范围和高化学和区域选择性.
  • 该方法已成功应用于格拉姆尺度合成和地点选择性标签.
  • 机理学研究为布伦斯特酸催化提供了洞察力.

结论:

  • 报告的策略提供了一个简单而通用的O-difluoroalkylhydroxylamines (FON) 的途径.
  • 这种方法促进了FON在多种分子架构中融入.
  • 机理学理解可能会使化化学和催化学的进一步进展成为可能.