A ruthenium-based catalytic system with switchable selectivity between cyclotrimerization and enyne metathesis/Diels-Alder reactions of terminal alkynes

Karabulut S., SARIASLAN B., ÖZTÜRK B. Ö.

CATALYSIS COMMUNICATIONS, vol.41, pp.12-16, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 41
  • Publication Date: 2013
  • Doi Number: 10.1016/j.catcom.2013.06.023
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.12-16
  • Keywords: Enyne metathesis, Diels-Alder reactions, One-pot synthesis, Switchable catalysis, 1,3-DIENE SYNTHESIS, CONSTRUCTION, ETHYLENE, BEARING
  • Hacettepe University Affiliated: Yes


In this study, we report a practical catalytic system, [RuCl2( p-cymene)](2)/IPr (IPr: 1,3-bis(2,6 diisopropylphenyl) imidazol-2-ylidene), that can switch between cyclotrimerization and cross enyne metathesis. The cyclotrimerization reaction of phenylacetylene catalyzed by [RuCl2(p-cymene)](2) can be switched to enyne metathesis by the introduction of a sterically hindered N-heterocyclic carbene. The 1,3-diene formed during this reaction reacts with dienophiles to form the Diels-Alder adduct. A practical one-pot synthesis method, utilizing enyne metathesis/Diels-Alder reactions, was used to construct cyclic compounds in an efficient manner. (C) 2013 The Authors. Published by Elsevier B.V. All rights reserved.