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Aminative Suzuki-Miyaura coupling.

Polpum Onnuch1, Kranthikumar Ramagonolla1, Richard Y Liu1

  • 1Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.

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Summary
This summary is machine-generated.

This study integrates nitrene insertion into Suzuki-Miyaura coupling, transforming C-C bond formation into C-N bond formation for diaryl amines. This novel approach unifies Suzuki-Miyaura and Buchwald-Hartwig coupling pathways for broader synthetic applications.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Suzuki-Miyaura coupling forms C-C bonds, while Buchwald-Hartwig coupling forms C-N bonds.
  • Existing methods often require distinct starting materials for C-C and C-N bond formation.

Purpose of the Study:

  • To develop a novel reaction that merges Suzuki-Miyaura and Buchwald-Hartwig coupling pathways.
  • To create diaryl amines from common starting materials via a unified catalytic process.

Main Methods:

  • Incorporation of a formal nitrene insertion process into the Suzuki-Miyaura reaction.
  • Utilized a palladium catalyst with a bulky ancillary phosphine ligand.
  • Employed a commercially available amination reagent.

Main Results:

  • Successfully altered Suzuki-Miyaura products from biaryls to C-N-C-linked diaryl amines.
  • Achieved efficient reactivity with various aryl halides, pseudohalides, boronic acids, and esters.
  • Demonstrated compatibility with diverse functional groups and heterocycles.

Conclusions:

  • The developed method effectively joins Suzuki-Miyaura and Buchwald-Hartwig coupling strategies.
  • Mechanistic studies revealed flexibility in bond-forming order, suggesting broad applicability.
  • Potential for expansion to new nucleophiles, electrophiles, and multi-component reactions was identified.