A convenient synthesis of functionalised 1-aryl-1,3-alkadiynes

Irina A. Balova, Victor N. Sorokoumov, Svetlana N. Morozkina, Olga V. Vinogradova, David W. Knight, Sergey F. Vasilevsky

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22 Citations (Scopus)

Abstract

A two-step, one-pot synthesis of functionalised 1-arylalka-1,3-diynes is described. A key feature in this approach is exploitation of the "acetylene zipper" reaction to obtain terminal 1,3-alkadiynes 3 from internal isomers 1. Without isolation, but after protonation, the 1,3-alkadiynes 3 are subjected to subsequent Pd/Cu-catalyzed Sonogashira cross-couplings with aryl iodides having both electron-withdrawing and electron-donating groups. The whole sequence takes place under mild reaction conditions to afford functionalised 1-aryl-alka-1,3-diynes 21-35 in high yields.

Original languageEnglish
Pages (from-to)882-888
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number5
DOIs
Publication statusPublished - 25 Feb 2005
Externally publishedYes

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Keywords

  • 1,3-Alkadienes
  • 1-Arylalka-1,3-diynes
  • Acetylene zipper
  • Cross-coupling
  • Rearrangement

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Balova, I. A., Sorokoumov, V. N., Morozkina, S. N., Vinogradova, O. V., Knight, D. W., & Vasilevsky, S. F. (2005). A convenient synthesis of functionalised 1-aryl-1,3-alkadiynes. European Journal of Organic Chemistry, (5), 882-888. https://doi.org/10.1002/ejoc.200400688