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Related Concept Videos

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.
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic rearrangements are...
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
[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.
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.

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Updated: Jul 3, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

Catalytic sequential reactions involving palladacycle-directed aryl coupling steps.

Marta Catellani1, Elena Motti, Nicola Della Ca'

  • 1Dipartimento di Chimica Organica e Industriale dell'Universita and CIRCC, Viale G. P. Usberti 17/A, Parma, Italy.

Accounts of Chemical Research
|August 6, 2008
PubMed
Summary

This study introduces a novel palladium-catalyzed method for selective aryl-aryl coupling using norbornene as a cooperative catalyst. This approach enables efficient C-C and C-H bond formation for synthesizing diverse aromatic and heteroaromatic compounds.

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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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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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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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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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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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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

Published on: February 16, 2020

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Palladium-catalyzed cross-coupling reactions are crucial for C-C bond formation.
  • The Suzuki reaction is a prominent method for aryl-aryl coupling.
  • Mild and selective catalytic methods are highly sought after in organic synthesis.

Purpose of the Study:

  • To develop a novel palladium-catalyzed sequential reaction for selective aryl-aryl coupling.
  • To utilize the cooperative action of palladium and norbornene for C-halide and C-H activation.
  • To synthesize diverse aromatic and heteroaromatic compounds via a regioselective approach.

Main Methods:

  • Employing palladium as an inorganic catalyst and norbornene as an organic catalyst.
  • Utilizing C-halide and C-H activation pathways.
  • Forming and manipulating palladacycle intermediates for controlled reactivity.
  • Sequential C-C and C-H bond formation using biphenylylpalladium species.
  • Synthesizing condensed heterocycles by replacing norbornene with an aryl-bonded aminocarbonyl group.

Main Results:

  • Achieved selective aryl-aryl coupling through cooperative Pd/norbornene catalysis.
  • Demonstrated regioselective arylation ortho to the C-halide bond via palladacycle intermediates.
  • Successfully synthesized biphenyl derivatives and a variety of aromatic and heteroaromatic compounds.
  • Formed biaryl-bonded Pd species for subsequent C-C, C-N, or C-O bond formation.
  • Obtained a key metallacycle for selective reaction direction, leading to diverse condensed heterocycles.

Conclusions:

  • The developed methodology offers a powerful tool for selective C-C and C-H bond formation.
  • Norbornene acts as a removable scaffold, facilitating controlled palladium-catalyzed reactions.
  • The approach enables the synthesis of complex aromatic and heteroaromatic structures with high diversity.