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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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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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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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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...
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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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.
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Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Catalytic, Directed C-C Bond Functionalization of Styrenes.

Shunsuke Onodera1, Ryo Togashi1, Soya Ishikawa1

  • 1Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.

Journal of the American Chemical Society
|April 7, 2020
PubMed
Summary

Researchers developed a new catalytic method to transform carbon-carbon bonds in styrene derivatives. This rhodium-catalyzed reaction efficiently converts alkenyl groups into new carbon substituents using various alkenes.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Carbon-carbon bond formation is fundamental to organic synthesis.
  • Styrene derivatives offer versatile platforms for chemical transformations.
  • Directing groups enable selective functionalization of organic molecules.

Purpose of the Study:

  • To develop a novel catalytic method for the conversion of C(aryl)-C(alkenyl) bonds.
  • To explore the reactivity of styrene derivatives with pyrazolyl directing groups.
  • To investigate the mechanism of C-C bond cleavage and formation.

Main Methods:

  • Utilized a rhodium catalyst for the C-C bond conversion.
  • Employed various alkenes, including styrenes, aliphatic alkenes, and allyl alcohols, as reaction partners.
  • Characterized reaction products using standard analytical techniques.

Main Results:

  • Efficient catalytic conversion of C(aryl)-C(alkenyl) bonds in styrene derivatives was achieved.
  • The alkenyl groups were successfully transformed into diverse carbon substituents.
  • The reaction demonstrated broad substrate scope with various alkenes.

Conclusions:

  • A new rhodium-catalyzed method for C-C bond formation in styrenes was established.
  • The developed methodology provides a powerful tool for synthesizing complex organic molecules.
  • The C-C bond cleavage likely proceeds through a hydrometalation/β-carbon elimination pathway.