Ruthenium-catalysed cross-coupling reaction of ketones with transformable directing groups as alkenyl electrophiles.

Chem Commun (Camb)

Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Technology, Hachioji, Tokyo 192-0982, Japan.

Published: October 2023

AI Article Synopsis

  • The study focuses on creating a new cross-coupling reaction using ruthenium as a catalyst to combine β-ketoamides with organoboronates.
  • This reaction involves breaking the alkenyl C-N bond of a compound called β-enaminoamide, which is formed by reacting β-ketoamide with pyrrolidine.
  • An amide directing group is essential in facilitating this reaction alongside the ruthenium catalyst.

Article Abstract

Herein, we report the development of ruthenium-catalysed cross-coupling reaction of β-ketoamides as alkenyl electrophiles with organoboronates. This reaction presumably proceeds the cleavage of the alkenyl C-N bond of the β-enaminoamide, which is generated from the β-ketoamide and pyrrolidine, and is promoted by a nearby amide directing group and a ruthenium catalyst.

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http://dx.doi.org/10.1039/d3cc04265kDOI Listing

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Ruthenium-catalysed cross-coupling reaction of ketones with transformable directing groups as alkenyl electrophiles.

Chem Commun (Camb)

October 2023

Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Technology, Hachioji, Tokyo 192-0982, Japan.

Article Synopsis
  • The study focuses on creating a new cross-coupling reaction using ruthenium as a catalyst to combine β-ketoamides with organoboronates.
  • This reaction involves breaking the alkenyl C-N bond of a compound called β-enaminoamide, which is formed by reacting β-ketoamide with pyrrolidine.
  • An amide directing group is essential in facilitating this reaction alongside the ruthenium catalyst.
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