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Chemoselective reactions of diazo compounds were achieved using rhodium(II) catalysis. This method enables the selective formation of diverse organic molecules and complex polycyclic N-heterocycles in a single step.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Donor/acceptor (D/A) and acceptor/acceptor (A/A) diazo moieties present synthetic challenges due to competing reactivity.
  • Controlling chemoselectivity in reactions involving multiple diazo groups within the same molecule is crucial for efficient synthesis.

Purpose of the Study:

  • To investigate the chemoselective reaction of D/A and A/A diazo moieties in a single molecule.
  • To explore the utility of rhodium(II) catalysis in controlling the reactivity of distinct diazo groups.
  • To develop a one-pot strategy for synthesizing polycyclic N-heterocycles.

Main Methods:

  • Utilized 3-diazo-1-(ethyl 2-diazomalonyl)indolin-2-one as a substrate.
  • Employed rhodium(II) catalysis to generate metal carbenoids.
  • Investigated various reaction pathways including insertion, cyclopropanation, and ylide formation/rearrangement.

Main Results:

  • Demonstrated preferential formation of a metal carbenoid from the D/A diazo group.
  • Achieved selective CH, NH, and OH insertion reactions, cyclopropanation, cyclopropenation, and sigmatropic rearrangements.
  • Successfully generated polycyclic N-heterocycles via tandem cascade sequences involving dipole formation and cycloaddition.
  • Observed excellent diastereoselectivity in intramolecular cycloadditions forming 5- to 7-membered rings.

Conclusions:

  • Rhodium(II) catalysis enables precise control over the chemoselective reactions of molecules bearing multiple diazo functionalities.
  • The developed methodology provides an efficient one-pot route to complex polycyclic N-heterocycles with high stereocontrol.
  • This approach offers a powerful tool for constructing intricate molecular architectures.