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Rhodium-Catalyzed Alkene Difunctionalization with Nitrenes.

Jennifer Ciesielski1, Geoffroy Dequirez1, Pascal Retailleau1

  • 1Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198, Gif-sur-Yvette, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 4, 2016
PubMed
Summary

Rhodium(II)-catalyzed reactions efficiently create 1,2-amino alcohols and 1,2-diamines from alkenes. These methods offer precise control for synthesizing pyrrolidines and vicinal amines.

Keywords:
aminationoxyaminationreaction mechanismsrhodiumsynthetic methods

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Organometallic Chemistry

Background:

  • Alkene functionalization is crucial for synthesizing complex organic molecules.
  • Developing catalytic methods for C-N bond formation remains an active area of research.

Purpose of the Study:

  • To investigate Rhodium(II)-catalyzed oxyamination and diamination of alkenes.
  • To elucidate the reaction mechanism, including intermediate species and transition states.

Main Methods:

  • Rhodium(II)-catalyzed reactions.
  • Experimental studies to determine reaction products and yields.
  • Density Functional Theory (DFT) calculations to model reaction pathways.

Main Results:

  • Oxyamination and diamination of alkenes proceeded in good to excellent yields with complete regiocontrol.
  • Intramolecular diamination efficiently produced pyrrolidines.
  • Intermolecular diamination yielded vicinal amines with orthogonal protecting groups.
  • DFT calculations supported a mechanism involving aziridination followed by nucleophilic ring opening via an Rh-bound nitrene.

Conclusions:

  • Rhodium(II) catalysis provides a versatile platform for alkene difunctionalization.
  • The proposed mechanism involving a metallanitrene intermediate is supported by computational and experimental data.
  • This work offers efficient synthetic routes to valuable nitrogen-containing compounds.