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

iScience

Michał Dąbrowski¹  Tomasz Nienałtowski²  Agata Tyszka-Gumkowska²  Vishal B. Purohit²  Anna Kajetanowicz²  Karol Grela² 

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

关键词: Chemistry;    Catalysis;    Organic chemistry;    Green chemistry;   

DOI  :  

来源: DOAJ

【 摘 要 】

Summary: 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.

【 授权许可】

Unknown