Effect of immobilization on catalytic characteristics of saturated Pd-N-heterocyclic carbenes in Mizoroki-Heck reactions

Aksin O., Turkmen H., Artok L., Cetinkaya B., Ni C., Buyukgungor O., ...More

JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol.691, no.13, pp.3027-3036, 2006 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 691 Issue: 13
  • Publication Date: 2006
  • Doi Number: 10.1016/j.jorganchem.2006.03.012
  • Journal Name: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.3027-3036
  • Keywords: Mizoroki-Heck reaction, C-C coupling, heterocyclic carbene, immobilized palladium, heterogeneous catalyst, palladium leaching, CROSS-COUPLING REACTIONS, MAIN-GROUP ELEMENTS, ARYL CHLORIDES, RECYCLABLE CATALYSTS, SUPPORTED PALLADIUM, OLEFIN METATHESIS, TRANSITION-METALS, MULTIPLE BONDS, IONIC LIQUIDS, COMPLEXES
  • Ondokuz Mayıs University Affiliated: No

Abstract

A saturated Pd-N-heterocyclic complex was immobilized on an amorphous silica. The complex itself is of very high thermal stability. However, TEM observations, hot filtration, reusability, and poisoning tests all revealed that the complex acted only as a precatalyst to highly active Pd species in Mizoroki-Heck reactions when immobilized. The complex appears more stable when used under homogeneous reaction conditions. The immobilized complex afforded high turnover numbers, 10(4)-10(5). The higher turnover frequencies were realized at the lower Pd concentrations, which is a characteristic property of ligand-free Pd catalyzed reactions. (c) 2006 Elsevier B.V. All rights reserved.