Rice University chemist Julian West and graduate students Yen-Chu Lu and Helen Jordan introduced a process for the rapid and scalable synthesis of fluoroketones precursors for drug design and manufacture that typically require a silver catalyst that have until now been challenging and expensive to make.
The lab's new, highly scalable process replaces silver with cerium-based ceric ammonium nitrate (CAN), which produces functional precursors under mild conditions in about 30 minutes whereas, the typical process is time consuming, has to be performed at high temperatures and done under a carefully controlled nitrogen or argon atmosphere.
Flourines are a great foothold to turn into an alkene or an aromatic ring," West said. “Replacing Hydrogen atoms in drug molecules with Fluorines via Cerium mediated C-C bond cleavage "is like armor plating at that position," he said. "That helps drugs last far longer in the body, so you don't have to take as much. That's desirable for chemotherapeutics." He noted that atorvastatin (aka Lipitor), one of the most commonly prescribed drugs in the United States, incorporates fluorine for the same purpose.
Reference:
Yen-Chu Lu et al, Rapid and scalable synthesis of fluoroketones via cerium-mediated C–C bond cleavage, Chemical Communications (2021).
DOI: 10.1039/D0CC08183C
Blog by: Pravajja Vaddikar
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