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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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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.
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Introduction
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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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.
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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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¹H NMR: Long-Range Coupling01:27

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The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
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Amino acid-derived bisphenolate palladium complexes as C-C coupling catalysts.

Eszter Fazekas1, David T Jenkins1, Andrew A Forbes1

  • 1Institute of Chemical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UK. r.mcintosh@hw.ac.uk.

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|November 22, 2021
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New palladium complexes with amine bisphenol (ABP) ligands, incorporating chiral amino acids, demonstrate efficient catalysis in Suzuki-Miyaura and Mizoroki-Heck C-C coupling reactions. These stable complexes offer a promising advancement in catalytic chemistry.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Amine bisphenol (ABP) pro-ligands were synthesized with chiral amino acid ester pendant arms.
  • The synthetic strategy minimized racemization during amino acid incorporation into the ABP scaffold.

Purpose of the Study:

  • To prepare novel palladium(II) complexes with an O,N,O pincer-like coordination mode.
  • To investigate the catalytic activity of these complexes in C-C coupling reactions.

Main Methods:

  • Preparation of ABP pro-ligands and their subsequent reaction with Pd(OAc)2.
  • Characterization of the resulting palladium complexes.
  • Evaluation of catalytic performance in Suzuki-Miyaura and Mizoroki-Heck coupling reactions.

Main Results:

  • Seven novel Pd(II) ABP complexes with distorted square-planar geometries were synthesized.
  • Complexes formed with pyridine as a base (LPd(py)) were air- and moisture-stable.
  • Catalytic Suzuki-Miyaura coupling achieved up to 81% yield with low catalyst loading (1 mol%) and mild temperatures (40 °C).
  • High activity was observed in the Mizoroki-Heck coupling of styrene and 4'-bromoacetophenone.

Conclusions:

  • Novel palladium(II) amine bisphenol complexes were successfully synthesized and characterized.
  • The developed catalysts exhibit excellent stability and high efficiency in key C-C coupling reactions.
  • These findings present a significant advancement in the field of homogeneous catalysis.