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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.3K
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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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

2.6K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.6K
Halogens03:01

Halogens

18.8K
Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
18.8K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.5K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
8.5K
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

18.7K
Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
18.7K
Halogenation of Alkenes02:46

Halogenation of Alkenes

16.1K
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.
16.1K

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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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Versatile Fluorine-Containing Building Blocks: β-CF3-1,3-enynes.

Mingqing Liu1, Zongxiang Yu1, Jingtong Li1

  • 1Department of Chemistry, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai 200241, China.

Molecules (Basel, Switzerland)
|December 23, 2022
PubMed
Summary

This review highlights the synthesis of valuable organofluorine compounds using beta-trifluoromethyl-1,3-enynes. These building blocks enable the creation of diverse molecules with biologically relevant structures.

Keywords:
diversity-oriented synthesis (DOS)fluorine-containing building blocksorganofluorine compoundsβ-CF3-1,3-enynes

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Area of Science:

  • Fluorine Chemistry
  • Organic Synthesis

Background:

  • Diversity-oriented synthesis is a key area in fluorine chemistry.
  • Beta-trifluoromethyl-1,3-enynes are versatile fluorine-containing building blocks.
  • These enynes exhibit unique reactivity for synthesizing complex molecules.

Purpose of the Study:

  • To review recent advancements in organofluorine compound synthesis.
  • To provide an overview of synthetic strategies utilizing beta-trifluoromethyl-1,3-enynes.
  • To highlight the preparation of biologically relevant trifluoromethylated and non-fluorinated compounds.

Main Methods:

  • Utilizing beta-trifluoromethyl-1,3-enynes as key synthons.
  • Employing various synthetic transformations to access diverse molecular scaffolds.
  • Focusing on reactions leading to O-, N-, and S-heterocycles, carboncycles, and polycycles.

Main Results:

  • Successful synthesis of numerous value-added organofluorine compounds.
  • Access to biologically relevant structural motifs including heterocycles and polycycles.
  • Demonstration of the utility of beta-trifluoromethyl-1,3-enynes in constructing complex architectures.

Conclusions:

  • Beta-trifluoromethyl-1,3-enynes are powerful building blocks in modern organic synthesis.
  • These synthons facilitate the efficient construction of diverse and valuable organofluorine compounds.
  • The reviewed synthetic methodologies offer broad applicability in medicinal and materials chemistry.