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Related Concept Videos

¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene π orbitals.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...
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

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Published on: November 9, 2019

Recent progress in coupling of two heteroarenes.

Dongbing Zhao1, Jingsong You, Changwei Hu

  • 1Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064, PR China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 21, 2011
PubMed
Summary

This review details four key coupling reactions for synthesizing biheteroaryl compounds, crucial for pharmaceuticals, materials, and natural products. These methods efficiently form heteroaryl-heteroaryl bonds, advancing synthetic chemistry.

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • The biheteroaryl motif is a fundamental structural unit in diverse applications, including pharmaceuticals, advanced materials, and natural products.
  • Efficient synthesis of heteroaryl-heteroaryl linkages is critical for accessing these valuable compounds.

Purpose of the Study:

  • To provide a comprehensive overview of modern synthetic strategies for constructing heteroaryl-heteroaryl bonds.
  • To highlight the versatility and applications of these coupling reactions in synthesizing complex molecules.

Main Methods:

  • Review of four major coupling reaction classes for biheteroaryl synthesis.
  • Discussion includes transition-metal-catalyzed couplings, direct C-H functionalization, oxidative C-H/C-H couplings, and decarboxylative cross-couplings.

Main Results:

  • Detailed examination of transition-metal-catalyzed coupling of heteroaryl halides/surrogates with heteroarylmetals.
  • Exploration of direct C-H heteroarylation of heteroarenes.
  • Analysis of oxidative C-H/C-H couplings and decarboxylative cross-couplings for biheteroaryl formation.

Conclusions:

  • The reviewed coupling reactions offer powerful and efficient routes for heteroaryl-heteroaryl bond formation.
  • These synthetic methodologies are vital for the development of new pharmaceuticals, materials, ligands, and natural product analogs.