Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions

Li M., Yuecel B., Adrio J., Bellomo A., Walsh P. J.

CHEMICAL SCIENCE, vol.5, no.6, pp.2383-2391, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 5 Issue: 6
  • Publication Date: 2014
  • Doi Number: 10.1039/c3sc53526f
  • Journal Name: CHEMICAL SCIENCE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2383-2391
  • Istanbul Technical University Affiliated: Yes

Abstract

Diarylmethylamines are of great interest due to their prevalence in pharmaceutical chemistry. As a result, new methods for their synthesis are in demand. Herein, we report a versatile protocol for the synthesis of diarylmethylamine derivatives involving palladium-catalyzed arylation of in situ generated 2-azaallyl anion intermediates. The 2-azaallyl anions are generated by reversible deprotonation of readily available aldimine and ketimine precursors. Importantly, the arylated aldimine and ketimine products do not undergo isomerization under the reaction conditions. Scale-up of the arylation and hydrolysis of the resulting products to furnish diarylmethylamines were also successfully performed.