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Related Concept Videos

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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

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

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...
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

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 strong interaction...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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.

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Updated: May 19, 2026

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
06:26

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

Published on: August 17, 2018

Transient Directing Group-Enabled Palladium-Catalyzed Axially Chiral C-H Alkynylation.

Yao-Yao Liu1,2,3,4, Yin-Xu Zhao1,2, Jia-Qi Chen3,4

  • 1State Key Laboratory of Coordination Chemistry, School of Chemistry, Nanjing University, Nanjing 210023, China.

Organic Letters
|May 18, 2026
PubMed
Summary

This study presents a new palladium-catalyzed method for creating chiral styrenes using transient directing groups. This approach offers high enantioselectivity and provides versatile chiral building blocks for further synthesis.

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

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Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
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Published on: August 17, 2018

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Area of Science:

  • Organic Chemistry
  • Asymmetric Synthesis
  • Catalysis

Background:

  • Accessing diverse atropisomers efficiently is a significant challenge in synthetic chemistry.
  • Developing modular and enantioselective synthetic strategies is crucial for producing valuable chiral molecules.

Purpose of the Study:

  • To develop an efficient and modular palladium-catalyzed enantioselective C-H alkynylation of styrene derivatives.
  • To utilize a transient directing group (TDG) strategy for the synthesis of axially chiral styrenes.
  • To explore the utility of computationally designed pyrrole-based chiral auxiliaries for stereochemical control.

Main Methods:

  • Palladium-catalyzed enantioselective C-H alkynylation reaction.
  • Transient directing group (TDG) strategy utilizing pyrrole-based chiral auxiliaries.
  • Computational studies to understand the mechanism of enantiodifferentiation.

Main Results:

  • High enantioselectivity in the synthesis of axially chiral styrenes under mild conditions.
  • Successful application of computationally designed pyrrole-based auxiliaries for TDG formation and stereocontrol.
  • Demonstration of the versatility of the resulting chiral aldehydes as precursors to chiral carboxylic acids and alcohols.

Conclusions:

  • The developed TDG strategy provides an efficient route to diverse axially chiral styrenes.
  • Computationally designed auxiliaries enhance rigidity and noncovalent interactions for effective enantiodifferentiation.
  • The synthesized chiral molecules, particularly carboxylic acids, serve as valuable ligands in asymmetric catalysis, showcasing broad synthetic potential.