Aryl trifluoromethyl sulfides (ArSCF3) are an important class of compounds in both the pharmaceutical and agrochemical areas owing to the capacity of SCF3 to act as a lipophilic electron-withdrawing group. Access to these compounds, however, is complicated by a lack of efficient, safe and general methods. Recent reports from our group regarding novel ligands such as BrettPhos and its analogs have allowed for the successful coupling of weak nucleophiles traditionally thought to be reluctant participants in a typical Pd(0)/(II) catalytic cycle. In light of this, we hypothesized that a similar system might allow for the formation of an aromatic C�SCF3 bond. By using the air and moisture stable AgSCF3 reagent and Ph(Et)3NI in the presence of catalytic amounts of Pd(0)/BrettPhos, we were able to convert a wide range of aryl and heteroaryl bromides into their corresponding aryl trifluoromethyl sulfides under mild conditions and in good to excellent yield.

Pd-catalyzed synthesis of Ar–SCF3 compounds under mild conditions

245th National Meeting (2013)

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