Synthesis of electrophilic N-heterocyclic carbenes based on azahelicene

Pierpaolo Morgante, Burjor Captain, Christopher D. Chouinard, Roberto Peverati, Norito Takenaka

Research output: Contribution to journalArticlepeer-review

Abstract

Helical-chiral analogues of imidazopyridine-2-yilidene were synthesized from 2-aza[6]helicene. The energies of their frontier orbitals were analyzed by the density functional theory calculations. The exceedingly large extension of NHC's π system by helicene annelation significantly enhanced the π electron-accepting properties of the carbene center while the strong σ electron-donating properties of imidazopyridine-2-yilidenes were retained.

Original languageEnglish (US)
Article number152143
JournalTetrahedron Letters
Volume61
Issue number30
DOIs
StatePublished - Jul 23 2020

Keywords

  • Catalyst design
  • Computational chemistry
  • Electronic properties
  • Helicene
  • N-heterocyclic carbenes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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