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Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n +...
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
12.1K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.5K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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5.0K
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...
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

3.3K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Expanding Access to Previously Inaccessible 5‑Membered N‑Heteroarynes.

Roman G Belli1, Jenna N Humke1, Sanu S Pullarat1

  • 1Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States.

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Summary

Researchers synthesized previously inaccessible heteroarynes using nickel-stabilized interactions and intramolecular Suzuki coupling. These novel compounds, including azaindole derivatives, enable new synthetic strategies and functionalizations.

Keywords:
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Area of Science:

  • Organic Chemistry
  • Heterocyclic Chemistry
  • Organometallic Chemistry

Background:

  • Previously reported synthesis of 7-aza-2,3-indolyne via nickel-stabilized intramolecular Suzuki coupling.
  • Unanswered questions regarding the electronic structure of the nickel-heteroaryne complex.

Purpose of the Study:

  • Investigate the electronic structure of nickel-stabilized heteroaryne complexes using XPS.
  • Expand the synthetic strategy to access new five-membered heteroarynes.
  • Identify factors influencing successful heteroaryne formation and explore their synthetic utility.

Main Methods:

  • X-ray photoelectron spectroscopy (XPS) for electronic structure analysis.
  • Intramolecular Suzuki coupling for heteroaryne synthesis.
  • Nuclear Magnetic Resonance (NMR) spectroscopy and X-ray crystallography for characterization.
  • Computational studies to justify experimental observations.

Main Results:

  • Successfully synthesized new classes of heteroarynes from indole, pyrrolopyrimidine, and azaindole isomers.
  • Demonstrated that aryne formation is dependent on the specific heteroarene.
  • Isolated and characterized a borate complex of 4-azaindole.
  • Showed that electron-donating substituents promote transmetalation in the 4-azaindole complex, supported by computational data.

Conclusions:

  • The study provides insights into the electronic structure and formation of nickel-stabilized heteroarynes.
  • A versatile strategy for accessing diverse five-membered heteroarynes was established.
  • The newly accessible heteroarynes serve as valuable building blocks for one-pot difunctionalization reactions.