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Related Concept Videos

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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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.
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Preparation of Alkynes: Alkylation Reaction02:27

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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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.
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Introduction
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Two precatalysts for application in propargylic CH activation.

Saskia Möller1, Hans Joachim Drexler1, Detlef Heller1

  • 1Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany.

Acta Crystallographica. Section C, Structural Chemistry
|October 8, 2019
PubMed
Summary

Rhodium complexes with a bis[(2-diphenylphosphanyl)phenyl] ether ligand serve as precatalysts for propargylic CH activation. A related inactive complex was also synthesized, highlighting potential reactivity in chloride-containing systems.

Keywords:
crystal structurehydrogen consumptionhydrogenationprecatalystspropargylic CH activationrhodium complex

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Rhodium complexes are crucial in catalysis.
  • Propargylic CH activation is an important synthetic transformation.
  • Redox-neutral and atomic-economic reactions are highly desirable.

Purpose of the Study:

  • To explore the use of specific rhodium complexes as precatalysts for propargylic CH activation.
  • To synthesize and characterize a related inactive rhodium complex.
  • To investigate the influence of chloride on rhodium complex speciation.

Main Methods:

  • Synthesis and characterization of rhodium(I) complexes with a bis[(2-diphenylphosphanyl)phenyl] ether ligand.
  • Application of these complexes as precatalysts in redox-neutral propargylic CH activation reactions.
  • Synthesis and characterization of a pentacoordinated rhodium(I) complex.

Main Results:

  • The rhodium(I) complexes [Rh(norbornadiene)(P-P)]BF4 and [Rh(COD)(P-P)]BF4 (P-P = bis[(2-diphenylphosphanyl)phenyl] ether) function as effective precatalysts for propargylic CH activation.
  • A catalytically inactive complex, [RhCl(norbornadiene)(P-P)], was synthesized.
  • The inactive complex can form in situ in the presence of chloride ions.

Conclusions:

  • The studied rhodium complexes are viable precatalysts for efficient propargylic CH activation.
  • The formation of an inactive species in the presence of chloride suggests careful control of reaction conditions is necessary.
  • This work contributes to the development of novel catalytic systems for organic synthesis.