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

Research output: Contribution to journalArticle

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

Fingerprint

Diynes
zippers
Acetylene
Electrons
Fasteners
Protonation
cross coupling
Iodides
synthesis
exploitation
acetylene
Isomers
iodides
isolation
electrons
isomers

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

A convenient synthesis of functionalised 1-aryl-1,3-alkadiynes. / Balova, Irina A.; Sorokoumov, Victor N.; Morozkina, Svetlana N.; Vinogradova, Olga V.; Knight, David W.; Vasilevsky, Sergey F.

In: European Journal of Organic Chemistry, No. 5, 25.02.2005, p. 882-888.

Research output: Contribution to journalArticle

Balova, IA, Sorokoumov, VN, Morozkina, SN, Vinogradova, OV, Knight, DW & Vasilevsky, SF 2005, 'A convenient synthesis of functionalised 1-aryl-1,3-alkadiynes', European Journal of Organic Chemistry, no. 5, pp. 882-888. https://doi.org/10.1002/ejoc.200400688
Balova, Irina A. ; Sorokoumov, Victor N. ; Morozkina, Svetlana N. ; Vinogradova, Olga V. ; Knight, David W. ; Vasilevsky, Sergey F. / A convenient synthesis of functionalised 1-aryl-1,3-alkadiynes. In: European Journal of Organic Chemistry. 2005 ; No. 5. pp. 882-888.
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