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

  • Minyan Li
  • , Baris Yücel
  • , Javier Adrio
  • , Ana Bellomo
  • , Patrick J. Walsh*
  • *Corresponding author for this work
  • University of Pennsylvania School of Arts and Sciences
  • Universidad Autónoma de Madrid

Research output: Contribution to journalArticlepeer-review

90 Citations (Scopus)

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. This journal is

Original languageEnglish
Pages (from-to)2383-2391
Number of pages9
JournalChemical Science
Volume5
Issue number6
DOIs
Publication statusPublished - Jun 2014

Funding

FundersFunder number
National Institute of General Medical Sciences104349
National Institutes of Health
National Stroke FoundationCHE-1152488

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