Carboxylic acid addition to terminal alkynes utilizing ammonium tagged Hoveyda-Grubbs catalyst supported on magnetically separable core/shell silica: A highly reusable and air compatible catalytic system


ÖZTÜRK B. Ö. , Gurcu D., Sehitoglu S. K.

JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol.883, pp.11-16, 2019 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 883
  • Publication Date: 2019
  • Doi Number: 10.1016/j.jorganchem.2019.01.005
  • Title of Journal : JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Page Numbers: pp.11-16
  • Keywords: Carboxylic acid, Alkyne, Ruthenium, Reusable catalyst, Enol-ester, ENOL ESTERS, MARKOVNIKOV ADDITION, GENERAL-SYNTHESIS, INTERNAL ALKYNES, AMINO-ACIDS, RUTHENIUM, METATHESIS, HYDROCARBOXYLATION

Abstract

In this study, the performance of ammonium tagged Hoveyda-Grubbs catalyst supported on magnetically separable core/shell silica gel was tested on carboxylic acid addition reactions to terminal alkynes using a variety of carboxylic acid derivatives under air atmosphere. The catalytic system was found to be compatible with air atmosphere and can tolerate even non-degassed solvents. The reaction parameters such as temperature, substrate/catalyst ratio and the effect of carboxylic acid on the selectivity and yield of the reaction were investigated in details. The reaction of arylacetylenes with acetic acid yielded the corresponding E-isomer with conversion values up to 99% with a catalytic loading of 1% Ru. The reusability of the catalyst was tested using acetic acid/benzoic acid and phenylacetylene in toluene at 85 degrees C under air atmosphere. The catalyst was found to be highly reusable and maintained its activity up to 11th run, reaching a conversion value of 83% with minimum ruthenium leaching. (C) 2019 Elsevier B.V. All rights reserved.