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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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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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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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A Versatile Palladium Synthon: [Pd(NHC)(PhC≡CPh)].

Francis Bru1, Mathieu Lesieur2, Albert Poater3

  • 1Department of Chemistry, Center for Sustainable Chemistry, Ghent University, Krijgslaan 281, 9000, Ghent, Belgium.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 1, 2022
PubMed
Summary

New palladium(0) complexes featuring N-heterocyclic carbene (NHC) ligands enable access to novel palladium species and catalyze allene hydrosilylation. These findings advance organometallic chemistry and catalytic applications.

Keywords:
alkyne ligandscarbene ligandshomogeneous catalysishydrosilylationpalladium

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Area of Science:

  • Organometallic Chemistry
  • Catalysis

Background:

  • Palladium complexes are crucial in catalysis.
  • Development of novel ligands and complexes is ongoing.

Purpose of the Study:

  • Synthesize and characterize new 14-electron palladium(0) complexes with NHC and diphenylacetylene ligands.
  • Explore their utility as synthons for other palladium species.
  • Investigate their application in the catalytic hydrosilylation of allenes.

Main Methods:

  • Synthesis and isolation of [Pd(NHC)(PhC≡CPh)] complexes.
  • Catalytic hydrosilylation reactions.
  • Density Functional Theory (DFT) calculations for electronic structure analysis.

Main Results:

  • Successful synthesis of 14-electron Pd(0)-NHC-alkyne complexes.
  • Demonstrated utility as precursors to Pd(0) and Pd(II) species.
  • Access to unprecedented mixed NHC-phosphite palladium(0) complexes.
  • Facile catalytic hydrosilylation of allenes achieved.
  • DFT revealed weak metal-alkyne interaction.

Conclusions:

  • The reported palladium(0) complexes are versatile synthons.
  • The NHC-alkyne motif facilitates allene hydrosilylation.
  • Understanding ligand interactions is key for catalyst design.