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Related Concept Videos

Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control01:23

Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control

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The addition of a hydrogen halide to 1,3-butadiene gives a mixture of 1,2- and 1,4-adducts. Since more substituted alkenes are more stable, the 1,4-adduct is expected to be the major product. However, the product distribution is strongly influenced by temperature; low temperature favors the 1,2-adduct, whereas the 1,4-adduct is predominant at high temperature.
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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
Oxymercuration-Reduction of Alkenes02:36

Oxymercuration-Reduction of Alkenes

9.2K
Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
9.2K
E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

12.2K
SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
12.2K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.5K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.5K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.5K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Related Experiment Video

Updated: Jan 7, 2026

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

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Dynamic Kinetic Control Enables Nickel-Catalyzed Enantioconvergent C(sp3)-O Coupling.

Jinze Du1, Xiaoying Fu1, Siming Xie1

  • 1State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing, 211198, P. R. China.

Journal of the American Chemical Society
|December 31, 2025
PubMed
Summary

This study introduces a nickel-catalyzed reaction for creating chiral C(sp3)-O bonds from racemic alkyl halides. The method achieves high selectivity and enables efficient synthesis of important pharmaceutical intermediates.

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Area of Science:

  • Organic Chemistry
  • Asymmetric Catalysis
  • Medicinal Chemistry

Background:

  • Enantioselective formation of C(sp3)-O bonds from racemic electrophiles is a significant challenge.
  • Existing methods often lack efficiency or require harsh conditions.

Purpose of the Study:

  • To develop a novel nickel(II)-catalyzed method for enantioselective C(sp3)-O bond formation.
  • To utilize dynamic kinetic resolution for efficient synthesis of enantioenriched compounds.

Main Methods:

  • Nickel(II)-catalyzed SN2 alkylation of racemic secondary alkyl halides with hydroxamic acids.
  • Exploitation of halide-driven substrate racemization under a dynamic kinetic resolution pathway.
  • Mild, air- and moisture-tolerant reaction conditions.

Main Results:

  • High enantioselectivity in the formation of hydroxamates.
  • Broad substrate scope, tolerating diverse electrophiles.
  • Successful gram-scale synthesis and derivatization.

Conclusions:

  • The developed protocol provides a versatile platform for late-stage, stereoselective C-O bond formation.
  • Enables concise access to bioactive molecules, including drug candidates like (S)-CCG-1423 and LY411575 intermediates.
  • Offers a valuable route to oxygen-containing motifs for drug discovery.