Oxime Palladacycle Supported on Magnetic Meoporous Silica: An Efficient Catalyst for Copper‐Free Acyl Sonogashira Reaction

Author:

Ghahramani Fatemeh1,Mansoori Yagoub12ORCID,John Michael3

Affiliation:

1. Department of Applied Chemistry Faculty of Science University of Mohaghegh Ardabili Daneshgah St. Ardabil Iran 56199-11367 Tel

2. Nanoscience and Nanotechnology Research Group University of Mohaghegh Ardabili Ardabil Iran 56199-11367

3. Georg-August-Universität Göttingen Institut für Anorganische Chemie Tammannstrasse 4 37077 Göttingen Germany

Abstract

AbstractThe catalytic activity of the supported bis(oxime palladacycle) catalyst was evaluated in the acyl Sonogashira reaction. The reaction conditions, such as solvent, base, and palladium content, were screened to achieve the best catalytic performance. Tetrahydrofuran (THF) solvent, triethylamine (Et3N) base, and the reaction temperature of 110 °C were found to be ideal for achieving high yields of the desired products. Furthermore, a catalyst loading of only 0.22 mol% palladium was sufficient to achieve good conversion. Broad ranges of aryl acetylenes and benzoyl chlorides were successfully coupled to give the desired acetylenic ketones. The reaction appeared to proceed efficiently using a small amount of catalyst. The magnetic property of the catalyst allowed for easy separation using an external magnet. The catalyst was stable and reused for multiple reaction runs without a significant deactivation. After seven cycles, the catalyst maintained over 90 % of its initial catalytic activity.

Funder

University of Mohaghegh Ardabili

Publisher

Wiley

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