Iridium-catalyzed ortho-C-H borylation of aromatic aldimines derived from pentafluoroaniline with bis(pinacolate)diboron.

Org Biomol Chem

Division of Chemical Process Engineering, Frontier Chemistry Center (FCC), Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan.

Published: April 2014

AI Article Synopsis

  • A new method for ortho-C-H borylation of aromatic aldimines from pentafluoroaniline was developed using an iridium catalyst.
  • The reaction occurs at a temperature of 120 °C and produces borylated products with high efficiency.
  • The iridium complex is created in the reaction mixture from specific precursors and works alongside 2-norbornene to achieve good regioselectivity.

Article Abstract

The development of an Ir-catalyzed ortho-C-H borylation of aromatic aldimines derived from pentafluoroaniline is reported. This reaction proceeded at 120 °C to afford the corresponding borylated products in high yield with good regioselectivity using an Ir complex formed in situ from [Ir(OMe)(cod)]2/2(C6F5)3P in the presence of 2-norbornene.

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Source
http://dx.doi.org/10.1039/c3ob42497aDOI Listing

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