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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.
10.2K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.2K
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.
8.2K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.1K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
6.1K
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

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

5.7K
The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
5.7K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.7K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
7.7K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

3.8K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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Direct C-H Arylation.

Jyoti Dhankhar1, Ilija Čorić2

  • 1Department of Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich.

Chimia
|December 9, 2023
PubMed
Summary

Transition metal catalysts enable selective C-H activation, replacing hydrogen with aryl groups. This approach simplifies complex organic synthesis by bypassing multistep sequences and activating strong C-H bonds.

Keywords:
C–H activationC–H arylationPalladiumSpatial anion control

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Carbon-hydrogen (C-H) bonds are ubiquitous in organic molecules.
  • Activating C-H bonds offers a direct route to complex molecular structures, potentially simplifying synthesis.
  • Transition metal catalysis provides a powerful strategy for controlled C-H bond functionalization.

Purpose of the Study:

  • To review recent advancements in mild and selective C-H activation reactions.
  • To highlight the replacement of C-H bonds with C-aryl groups.
  • To emphasize the contribution of the authors' group to this field.

Main Methods:

  • Utilizing transition metal catalysts for C-H bond activation.
  • Developing strategies for selective functionalization of strong C-H bonds.
  • Focusing on catalytic C-H arylation reactions.

Main Results:

  • Demonstrated methods for activating typically unreactive C-H bonds.
  • Achieved site-selectivity in C-H functionalization, differentiating similar C-H bonds.
  • Showcased the successful replacement of C-H bonds with C-aryl groups.

Conclusions:

  • Transition metal-catalyzed C-H activation is a key strategy for efficient organic synthesis.
  • Selective C-H arylation offers a powerful tool for constructing complex molecules.
  • Continued research in this area promises further advances in synthetic methodology.