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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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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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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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Intermolecular Allene Functionalization by Silver-Nitrene Catalysis.

Manuel R Rodríguez1, María Besora2, Francisco Molina1

  • 1Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Quı́mica Sostenible and Departamento de Quı́mica, Universidad de Huelva, 21007 Huelva, Spain.

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|June 28, 2020
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Silver catalysis enables efficient intermolecular nitrene transfer to allenes, yielding azetidines from arylallenes and aziridines from alkylallenes. These products can be further transformed into valuable aminocyclopropanes.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Metal-mediated nitrene transfer reactions are crucial for nitrogen-containing compound synthesis.
  • Allenes are versatile substrates in organic synthesis, but their reactivity with nitrene transfer agents is less explored.
  • Developing efficient catalytic systems for nitrene transfer to allenes remains a synthetic challenge.

Purpose of the Study:

  • To report the first efficient metal-mediated intermolecular nitrene transfer to allenes.
  • To investigate the influence of allene substituents on the reaction outcome.
  • To elucidate the reaction mechanism and explore synthetic applications of the resulting products.

Main Methods:

  • Utilized a silver catalyst precursor, [Tp*,BrAg]2, for mediating the reaction.
  • Employed PhI═NTs as the nitrene source.
  • Conducted mechanistic studies to understand the reaction pathways.
  • Explored subsequent synthetic transformations of the azetidine and aziridine products.

Main Results:

  • Achieved efficient silver-catalyzed intermolecular nitrene transfer to allenes.
  • Demonstrated substituent-dependent product formation: arylallenes yielded azetidines, while alkylallenes produced methylene aziridines.
  • Proposed mechanistic pathways involving cyclopropylimine intermediates for azetidine formation and direct nitrene addition for aziridines.
  • Showcased the utility of the synthesized azetidines and aziridines for further conversion into aminocyclopropanes.

Conclusions:

  • Established a novel silver-catalyzed method for nitrene transfer to allenes.
  • Highlighted the critical role of allene substituents in directing the reaction outcome.
  • Provided a versatile synthetic route to azetidines, aziridines, and aminocyclopropanes.