High Turnover Number and Rapid, Room-Temperature Amination of Chloroarenes Using Saturated Carbene Ligands

  • 10.1021/ol005751k
  • Organic Letters
  • p 1423-1426, Volume 2, Issue 10,
  • journal-article
A catalytic system for the mild amination of aryl chlorides is described. This system consists of a Pd(0) precursor and a dihydroimidazoline carbene ligand, which is generated in situ from its protonated tetrafluoroborate salt (2). Using this catalyst, aryl and heteroaryl chlorides react with secondary amines and anilines within hours at room temperature. Turnover numbers as high as 5000 are obtained at elevated temperatures for reaction of morpholine with an unactivated aryl chloride.


Reproducible Catalyst System

I need prepare a series of 2-amino-pyridines around 2003, and found this paper by SciFinder. 

I tested the reaction of 1-Boc-piperidine and 2-chloro-3-methyl- pyridine in 50mg scale using 5 mmol% catalysts.

The reactions were not completed in 3h at rt.  When the mixture...