Palladium-Catalyzed Decarbonylative Coupling of (Hetero)Aryl Boronate Esters with Difluorobenzyl Glutarimides.

Org Lett

Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States.

Published: October 2023

AI Article Synopsis

  • The report details a method for Pd-catalyzed decarbonylative coupling, using difluorobenzyl glutarimides and (hetero)aryl boronate esters to create new difluorobenzyl-substituted (hetero)arene compounds.
  • The phosphine ligand PAdBu and neopentylboronate ester nucleophiles are crucial for achieving selective product formation, specifically avoiding the production of difluorobenzyl ketones.
  • This coupling reaction is applicable to a wide range of (hetero)aryl boronate esters and difluorobenzyl glutarimides, demonstrating its versatility.

Article Abstract

This report describes the Pd-catalyzed decarbonylative coupling of difluorobenzyl glutarimides with (hetero)aryl boronate esters to yield difluorobenzyl-substituted (hetero)arene products. The use of PAdBu as the phosphine ligand in combination with neopentylboronate ester nucleophiles proved critical for the selective formation of the decarbonylative coupling product versus analogous difluorobenzyl ketone. This transformation is effective for electronically diverse (hetero)aryl boronate esters and substituted difluorobenzyl glutarimides.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10629228PMC
http://dx.doi.org/10.1021/acs.orglett.3c03071DOI Listing

Publication Analysis

Top Keywords

decarbonylative coupling
12
heteroaryl boronate
12
boronate esters
12
difluorobenzyl glutarimides
12
palladium-catalyzed decarbonylative
4
coupling heteroaryl
4
difluorobenzyl
4
esters difluorobenzyl
4
glutarimides report
4
report describes
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!