Convergent Azaspirocyclization of Bromoarenes with N-Tosylhydrazones by a Palladium Catalyst

Aika Yanagimoto, Yota Uwabe, Qikun Wu, Kei Muto, Junichiro Yamaguchi*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

1-Azaspirocyclic compounds have gained attention in chemistry and drug discovery fields. In this manuscript, the development of a Pd-catalyzed dearomative azaspirocyclization of bromoarenes bearing an aminoalkyl group with N-tosylhydrazones is described. The present method enables azaspirocyclization with the introduction of carbon substituents, achieving the convergent synthesis of 1-azaspirocycles. This method allowed furan, thiophene, and naphthalene cores to generate the corresponding 1-azaspirocycles. The obtained azaspirocycles from furans were further elaborated via an acid-catalyzed rearrangement to afford 1-azaspirocyclopentenones.

Original languageEnglish
Pages (from-to)10429-10435
Number of pages7
JournalACS Catalysis
Volume11
DOIs
Publication statusPublished - 2021

Keywords

  • bromoarenes
  • dearomatization
  • palladium
  • Pd-carbene
  • spirocyclic compounds

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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