Silver-Mediated Trifluoromethylation of Arenes Using TMSCF3

Introduction of the trifluoromethyl moiety into aromatic rings.

And now by Sanford et al. (University of Michigan, USA), another contestant in the trifluoromethylation ring: TMSCF3. The authors describe a method suitable for medchem, using the above mentioned reagent, AgOTf and KF. Though only one equivalent of the trifluoromethylation reagent is needed, four equivalents of the two other salts are required. In the 15 examples reported the selectivity is the main issue (in the end it is an electrophilic substitution reaction), but the yields are very good and three examples with heterocycles are included. Maybe not the definitive trifluoromethylation method, but it is easy and cheap, so give it a try the next time you need one of these.

Org. Lett., Article ASAP. See: 10.1021/ol202174a