1,2-Diamination of Alkenes via 1,3-Dipolar Cycloaddition with Azidium Ions or Azides

Setareh Saryazdi, Sean Parkin, Robert B. Grossman

Research output: Contribution to journalArticlepeer-review

2 Scopus citations


We describe two new methods for the 1,2-diamination of alkenes. First, either an azidium ion (ArN═N+═NAr) undergoes 1,3-dipolar cycloaddition with an alkene to give a 1,2,3-triazolinium ion directly, or an intramolecular azide-alkene cycloaddition followed by N-benzylation provides the same. Second, hydrogenation of the 1,2,3-triazolinium ion over Raney Ni excises the central N atom and gives the 1,2-diamine. The stereochemistry of the alkene is usually, but not always, preserved in the 1,2-diamine.

Original languageEnglish
Pages (from-to)331-335
Number of pages5
JournalOrganic Letters
Issue number2
StatePublished - Jan 20 2023

Bibliographical note

Funding Information:
S.S. thanks the University of Kentucky (UK) Department of Chemistry for two RCTF fellowships. The authors thank Prof. Steven Van Lanen and Hoda Saghaian (UK Department of Pharmaceutical Sciences) for allowing us to use their LC-MS instrument.

Publisher Copyright:
© 2023 American Chemical Society.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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