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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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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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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 para...
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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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Coupling dinitrogen and hydrocarbons through aryl migration.

Sean F McWilliams1, Daniël L J Broere1,2, Connor J V Halliday3

  • 1Department of Chemistry, Yale University, New Haven, CT, USA.

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Summary

Researchers developed an iron catalyst system that activates abundant hydrocarbons and atmospheric nitrogen (N2) to create aniline derivatives. This breakthrough enables the direct coupling of N2 with hydrocarbons, paving the way for new catalytic methods.

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Area of Science:

  • * Inorganic Chemistry
  • * Catalysis
  • * Organometallic Chemistry

Background:

  • * Activating inert molecules like hydrocarbons and atmospheric nitrogen (N2) is a significant challenge in chemistry.
  • * Traditional methods for forming carbon-nitrogen bonds from N2 require reactive organic precursors incompatible with reductive conditions needed for N2 activation, hindering catalytic applications.

Purpose of the Study:

  • * To report a novel diketiminate-supported iron system capable of sequentially activating benzene and N2.
  • * To demonstrate a one-pot conversion of petroleum-derived arenes into silylated aniline derivatives using N2 as the nitrogen source.

Main Methods:

  • * Employed a diketiminate-supported iron bromide complex.
  • * Utilized a reaction mixture including sodium powder, crown ether, trimethylsilyl bromide, and N2.
  • * Isolated and characterized intermediate compounds along the reaction pathway.

Main Results:

  • * Successfully coupled benzene and N2 to form aniline derivatives via a sequential activation mechanism.
  • * Achieved a one-pot conversion of various arenes into silylated anilines.
  • * Identified and characterized key intermediates, supporting a proposed reaction mechanism.

Conclusions:

  • * The developed iron system enables the direct coupling of atmospheric nitrogen with abundant hydrocarbons.
  • * This strategy offers a new route for synthesizing aniline derivatives and advances the development of catalytic systems for N2 functionalization.