Synthesis and Reactivity of a Terminal 1-Alkynyl Triazene

J Org Chem. 2022 Dec 16;87(24):16882-16886. doi: 10.1021/acs.joc.2c02121. Epub 2022 Dec 2.

Abstract

1-Alkynyl triazenes are versatile reagents in synthetic organic chemistry, but the structural diversity of this compound class has so far been limited. Herein, we describe the synthesis of a terminal 1-alkynyl triazene. Subsequent functionalization allows the preparation of 1-alkynyl triazenes with a range of functional groups including esters, alcohols, cyanides, phosphonates, and amides. Furthermore, the terminal 1-alkynyl triazene can be used for the synthesis of di- and triynes and for the preparation of (hetero)aromatic triazenes in metal-catalyzed cyclization reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols*
  • Amides / chemistry
  • Cyclization
  • Molecular Structure
  • Triazenes* / chemistry

Substances

  • Triazenes
  • Alcohols
  • Amides