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Related Concept Videos

Coupled Reactions01:17

Coupled Reactions

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Cellular processes such as building and breaking down complex molecules occur through stepwise chemical reactions. Some of these chemical reactions are spontaneous and release energy, whereas others require energy to proceed. Cells often couple the energy-releasing reaction with the energy-requiring one to carry out important cell functions. 
Energy in adenosine triphosphate or ATP molecules is easily accessible to do work. ATP powers the majority of energy-requiring cellular reactions....
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Base-Catalyzed Aldol Addition Reaction01:08

Base-Catalyzed Aldol Addition Reaction

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As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.
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Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

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The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
3.3K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.3K
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.
2.3K
Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

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

1.7K
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...
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Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)01:22

Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)

1.5K
Vicinal or three-bond coupling is commonly observed between protons attached to adjacent carbons. Here, nuclear spin information is primarily transferred via electron spin interactions between adjacent C‑H bond orbitals. This generally favors the antiparallel arrangement of spins, so 3J values are usually positive.
The extent of coupling depends on the C‑C bond length, the two H‑C‑C angles, any electron-withdrawing substituents, and the dihedral angle between the involved orbitals. The...
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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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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Gold Catalyzed Multicomponent Reactions beyond A³ Coupling.

Renso Visbal1, Sara Graus2, Raquel P Herrera3

  • 1Departamento de Ciencias Naturales y Exactas, Universidad de la Costa, Calle 58 #55-66, 080002 Barranquilla, Colombia. rvisbal4@cuc.edu.co.

Molecules (Basel, Switzerland)
|September 6, 2018
PubMed
Summary

This review highlights gold-catalyzed multicomponent reactions for creating complex molecular structures. These reactions offer efficient pathways to diverse compounds with potential biological activity, advancing organic synthesis.

Keywords:
1,4-dihydropyridines3,4-dihydropyrimidin-2(1H)-onesbutenolidescatalysisethersgoldmulticomponent reactionsoxazolespyridinesspirocyclesthiazolo-quinolinesβ-alkoxyketones

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Area of Science:

  • Organic Synthesis
  • Medicinal Chemistry
  • Catalysis

Background:

  • The synthesis of complex molecular architectures is crucial for discovering new drugs and materials.
  • Multicomponent reactions (MCRs) provide an efficient strategy for building molecular complexity and diversity in a single step.
  • Gold catalysis has emerged as a powerful tool in organic synthesis, enabling novel transformations.

Purpose of the Study:

  • To review significant advancements in gold-catalyzed multicomponent reactions over the last decade.
  • To showcase the application of these reactions in synthesizing complex molecular skeletons.
  • To highlight the relevance of these skeletons in the development of biologically active compounds.

Main Methods:

  • Literature review focusing on gold-catalyzed multicomponent reactions published in the last 10 years.
  • Analysis of reaction mechanisms and scope.
  • Identification of key structural motifs and their biological relevance.

Main Results:

  • Compilation of diverse gold-catalyzed MCRs yielding complex molecular frameworks.
  • Demonstration of the efficiency and atom-economy of these synthetic strategies.
  • Examples of synthesized compounds exhibiting significant biological activities.

Conclusions:

  • Gold-catalyzed multicomponent reactions are highly effective for constructing complex organic molecules.
  • These reactions provide rapid access to diverse chemical entities for drug discovery and development.
  • Continued exploration of gold catalysis in MCRs promises further innovation in synthetic chemistry.