Chemistry

Chemists discover streamlined method to attach fluorine-containing groups to molecules

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This study describes a new method for installing trifluoromethylthio (SCF3) and trifluoromethoxy (OCF3) groups onto aromatic compounds at late stages of synthesis. The researchers combined continuous flow chemistry to generate reactive anions with aryl thianthrenium salts as coupling partners, enabling efficient functionalization of complex molecules. This approach offers improved safety and practicality compared to traditional methods by generating hazardous reagents in situ under controlled flow conditions.


Trifluoromethyl-containing groups are highly valuable in pharmaceuticals and agrochemicals due to their effects on molecular properties like metabolic stability and lipophilicity. This methodology provides chemists with a safer and more practical tool for introducing these important functional groups into drug candidates and other bioactive molecules at late synthetic stages, potentially accelerating development timelines.


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Journal of the American Chemical Society
DOI: 10.1021/jacs.6c04790

Source: [ASAP] Late-Stage Aryl NCF3 and SCF3 Installation Enabled by Coupling Flow-Generated Anions with Aryl Thianthrenium Salts