Nickel-Catalyzed N,N-Diarylation of 8-Aminoquinoline with Large Steric Aryl Bromides and Fluorescence of Products.

A simple and efficient methodology for the synthesis of large sterically hindered triarylamines in a single step was developed. A direct N,N-diarylation of 8-aminoquinoline with sterically hindered bromides, making use of inexpensive nickel as a catalyst and simple sodium salt as a base, gives the products in good to excellent yields. Various bromides and substituted 8-aminoquinolines are tolerated. Preliminary fluorescence results indicate that these sterically hindered and conjugated triarylamines may have some potential in material chemistry.