Testing enabling techniques for olefin metathesis reactions of lipophilic substrates in water as a diluent

Agata Tyszka-Gumkowska; Vishal B Purohit; Tomasz Nienałtowski; Michał Dąbrowski; Anna Kajetanowicz; Karol Grela

doi:10.1016/j.isci.2022.104131

Testing enabling techniques for olefin metathesis reactions of lipophilic substrates in water as a diluent

iScience. 2022 Mar 21;25(4):104131. doi: 10.1016/j.isci.2022.104131. eCollection 2022 Apr 15.

Authors

Agata Tyszka-Gumkowska¹, Vishal B Purohit¹, Tomasz Nienałtowski^{1

2}, Michał Dąbrowski¹, Anna Kajetanowicz¹, Karol Grela¹

Affiliations

¹ Biological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, Poland.
² Polpharma SA Pharmaceutical Works, Pelplińska 19, 83-200 Starogard Gdański, Poland.

Abstract

Olefin metathesis reactions of diverse polyfunctional substrates were conducted in water emulsions using two hydrophobic ruthenium catalysts in the presence of air. Instead of using surfactants to increase the efficiency of the metathesis reaction in water, ultrasound and microwave techniques were tested on a small-scale reaction, whereas conventional heating and mechanical stirring were effective enough to provide high conversion and selectivity on a larger scale. The developed conditions extend known protocols for the aqueous metathesis methodology, utilizing relatively low catalyst loadings and allowing for simple product isolation and purification. The established synthetic protocol was successfully adopted in the large-scale synthesis of a pharmaceutically related product - sildenafil (Viagra) derivative.

Keywords: Catalysis; Chemistry; Green chemistry; Organic chemistry.