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Related Concept Videos

Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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 confirmed through isotopic...
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
Halogenation of Alkenes02:46

Halogenation of Alkenes

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.
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
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Published on: December 16, 2019

A mild benzannulation through directed cycloaddition reactions.

James D Kirkham1, Roger J Butlin, Joseph P A Harrity

  • 1Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, UK.

Angewandte Chemie (International Ed. in English)
|May 18, 2012
PubMed
Summary
This summary is machine-generated.

Alkynyl borane cycloadditions offer a mild and efficient method for synthesizing aromatic difluoroboranes. These compounds can be easily converted into various valuable products, simplifying complex chemical transformations.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Traditional methods for synthesizing aromatic difluoroboranes are often harsh and inefficient.
  • Developing milder and more efficient synthetic routes is crucial for advancing organic synthesis.

Purpose of the Study:

  • To develop a novel, substrate-directed alkynyl borane cycloaddition reaction.
  • To establish an efficient and mild method for the synthesis of aromatic difluoroboranes.

Main Methods:

  • Utilizing alkynyl borane cycloaddition reactions.
  • Employing substrate-directed synthesis strategies.
  • Exploring the transformation of synthesized aromatic boranes into diverse products.

Main Results:

  • Achieved substrate-directed assembly of aromatic difluoroboranes.
  • Demonstrated an extremely mild and efficient reaction manifold.
  • Showcased the facile conversion of aromatic boranes into a range of useful products.

Conclusions:

  • Alkynyl borane cycloadditions provide a superior alternative to traditional methods for synthesizing aromatic difluoroboranes.
  • The developed method offers a versatile platform for accessing valuable boron-containing organic compounds.