Base-stabilized nitrilium ions as convenient imine synthons

Tom Van Dijk, Martijn S. Bakker, Flip Holtrop, Martin Nieger, J. Chris Slootweg, Koop Lammertsma

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)


A simple and efficient methodology is presented for the synthesis of a wide range of substituted imines. It is based on stabilizing readily available, but thermally labile, N-alkylnitrilium triflates with pyridine or DMAP to moderately air-stable adducts. These base-stabilized imine synthons react conveniently with phosphorus- and nitrogen-based nucleophiles to amidines and phosphaamidines.

Original languageEnglish
Pages (from-to)1461-1464
Number of pages4
JournalOrganic Letters
Issue number6
Publication statusPublished - 20 Mar 2015
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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