Design and synthesis of 3,3′-triazolyl biisoquinoline N,N’-dioxides via Hiyama cross-coupling of 4-trimethylsilyl-1,2,3-triazoles

Shiyu Sun, Carlyn Reep, Chenrui Zhang, Burjor Captain, Roberto Peverati, Norito Takenaka

Research output: Contribution to journalArticlepeer-review

Abstract

A new strategy to effectively lock the conformation of substituents at the 3,3′-positions of axial-chiral biisoquinoline N,N’-dioxides was developed based on the strong dipole–dipole interaction between 1,2,3-triazole and pyridine N-oxide rings. The crystal structure and the DFT calculations of 3,3′-bis(1-benzyl-1H-1,2,3-triazole-4-yl)-1,1′-biisoquinoline N,N’-dioxide (3a) provided strong support for this strategy. Furthermore, we successfully demonstrated that readily available 4-trimethylsilyl-1,2,3-triazoles are viable nucleophiles for Hiyama cross-coupling.

Original languageEnglish (US)
Article number153338
JournalTetrahedron Letters
Volume81
DOIs
StatePublished - Sep 28 2021

Keywords

  • 1,2,3-triazoles
  • axial-chiral Lewis bases
  • Catalyst design
  • Computational chemistry
  • Hiyama cross-coupling

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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