One-pot synthesis of alpha,beta-unsaturated ketones through sequential alkyne dimerization/hydration reactions using the Hoveyda-Grubbs catalyst

ÖZTÜRK B. Ö., Sariaslan B., Askun M., Tunali Z., KARABULUT ŞEHİTOĞLU S.

NEW JOURNAL OF CHEMISTRY, vol.45, pp.16689-16695, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 45
  • Publication Date: 2021
  • Doi Number: 10.1039/d1nj02410h
  • Journal Name: NEW JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Biotechnology Research Abstracts, Chemical Abstracts Core, Chimica, Compendex, EMBASE, DIALNET
  • Page Numbers: pp.16689-16695
  • Hacettepe University Affiliated: Yes

Abstract

Herein we report a sequential one-pot alkyne dimerization/hydration protocol for the regioselective synthesis of alpha,beta-unsaturated ketones in quantitative yields. The alkyne dimerization reactions of terminal arylacetylenes proceeded with high regioselectivity in the presence of the Hoveyda-Grubbs 2nd generation catalyst (1 mol%) and tricyclohexylphosphine (4 mol%). The hydration reactions of in situ formed 1-aryl-3-en-1-ynes proceeded very rapidly in the presence of CCl3COOH/p-TsOH center dot H2O, yielding the corresponding unsaturated ketones within 15 minutes in quantitative yields. Different arylacetylene derivatives were converted to the corresponding alpha,beta-unsaturated ketones in quantitative yields (94-95%) using sequential one-pot alkyne dimerization/hydration reactions.