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Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.5K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.5K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.8K
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...
3.8K
Radical Formation: Addition00:47

Radical Formation: Addition

2.1K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
2.1K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.2K
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.
2.2K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.5K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.5K
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

2.1K
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
2.1K

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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Asymmetric Ni-Catalyzed Radical Relayed Reductive Coupling.

Xiaofeng Wei1, Wei Shu1, Andrés García-Domínguez1

  • 1Department of Chemistry, University of Zurich, Winterthurerstrasse 190, Zurich, CH 8057, Switzerland.

Journal of the American Chemical Society
|June 30, 2020
PubMed
Summary
This summary is machine-generated.

This study introduces a novel nickel-catalyzed asymmetric reductive dicarbofunctionalization of alkenes. This method efficiently creates chiral aliphatic structures using readily available halides and olefins with high stereoselectivity.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Alkene dicarbofunctionalization is crucial for synthesizing aliphatic compounds.
  • Catalytic asymmetric variants for this transformation are limited.
  • Reductive cross-coupling strategies offer potential advantages.

Purpose of the Study:

  • To develop a highly efficient asymmetric intermolecular nickel-catalyzed reductive dicarbofunctionalization of alkenes.
  • To enable the simultaneous addition of Csp2- and Csp3-halides across various olefins.
  • To achieve high regio- and enantioselectivity in the synthesis of chiral building blocks.

Main Methods:

  • Utilized a nickel-catalyzed reductive dicarbofunctionalization approach.
  • Employed readily available Csp2- and Csp3-halides as electrophiles.
  • Investigated the reaction with vinyl amides, vinyl boranes, and vinyl phosphonates at room temperature.
  • Leveraged an in situ generated chiral alkyl Ni(III)-intermediate for stereocontrol.

Main Results:

  • Achieved highly regio- and enantioselective dicarbofunctionalization of alkenes.
  • Demonstrated the simultaneous addition of two distinct electrophiles across olefins.
  • Successfully employed an (l)-(+)-isoleucine chiral bisoxazoline ligand for stereodefined Csp3-Csp2 bond formation.
  • Showcased the synthesis of chiral amides through asymmetric radical relayed reductive couplings (ARRRCs).

Conclusions:

  • Presented a novel and efficient asymmetric intermolecular nickel-catalyzed reductive dicarbofunctionalization of alkenes.
  • Highlighted the synthetic utility of the methodology for assembling chiral building blocks like amines and oxazolines.
  • Established a new pathway for stereocontrolled Csp3-Csp2 bond formation without sensitive organometallic reagents.