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Related Concept Videos

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

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

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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...
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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.
11.9K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.2K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.2K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.3K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.3K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

3.6K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.6K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.6K
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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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Iodane-Guided ortho C-H Allylation.

Wei W Chen1,2, Anton Cunillera1, Dandan Chen3,4

  • 1Dept. of Biological Chemistry, Centro de Innovación en Química Avanzada (ORFEO-CINQA), Institute of Advanced Chemistry of Catalonia (IQAC-CSIC), c/Jordi Girona 18-26, 08034, Barcelona, Spain.

Angewandte Chemie (International Ed. in English)
|July 29, 2020
PubMed
Summary

A novel metal-free C-H allylation method creates functionalized ortho-allyl-iodoarenes using hypervalent iodine and allylsilanes. This versatile strategy enables the synthesis of complex molecules, including the antimitotic agent Dosabulin.

Keywords:
C−H functionalizationallylic compoundsareneshypervalent compoundsrearrangements

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology

Background:

  • Developing efficient C-H functionalization strategies is crucial for streamlined synthesis.
  • Metal-free catalytic systems are highly desirable for sustainability and cost-effectiveness.

Purpose of the Study:

  • To introduce a novel metal-free C-H allylation reaction for synthesizing ortho-allyl-iodoarenes.
  • To demonstrate the broad substrate scope and utility of the developed method.

Main Methods:

  • Utilizing hypervalent (diacetoxy)iodoarenes and allylsilanes.
  • Employing an iodane-guided "iodonio-Claisen" allyl transfer mechanism.
  • Characterizing products and elucidating reaction mechanism via DFT calculations.

Main Results:

  • Successful synthesis of diverse functionalized ortho-allyl-iodoarenes.
  • Broad substrate scope, including electron-neutral and electron-poor arenes.
  • Demonstrated utility in a concise synthesis of the Dosabulin antimitotic core.

Conclusions:

  • The developed metal-free C-H allylation is an efficient and versatile method for accessing valuable ortho-allylated iodoarene building blocks.
  • The reaction proceeds via a unique iodonio-Claisen rearrangement, offering insights into transition-state structures and stereoselectivity.
  • This strategy provides a powerful tool for organic synthesis, particularly in the construction of complex bioactive molecules.