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When chemists want to tweak the properties of an aromatic or heteroaromatic molecule, they often gussy it up with a trifluoromethyl group. The CF3 substituent is known to alter solubility and improve the activity of drugs. There are several ways to append CF3 groups to the rings, but no existing process is without its flaws. Some produce a variety of regioisomers. Others require reagents that are tricky to work with. Seeking to provide chemists with a simple and scalable trifluoromethylation method, MIT chemists Stephen L. Buchwald and Mao Chen combined their expertise in trifluoromethylation with their know-how in flow chemistry, where reactions are run via a continuous stream instead of in a batch. They’ve come up with a process that can make trifluoromethylated aromatics and heteroaromatics in a matter of minutes (Angew. Chem. Int. Ed. 2013, DOI: 10.1002/anie.201306094). The copper-mediated cross-coupling reaction uses aryl iodides as starting materials and inexpensive and easy-to-handle potassium trifluoroacetate as a CF3 source.
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