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

4 Scopus citations

Abstract

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
Volume25
Issue number2
DOIs
StatePublished - Jan 20 2023

Bibliographical note

Publisher Copyright:
© 2023 American Chemical Society.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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