Abstract
A Sandmeyer type process is disclosed that allows the straightforward synthesis of pentafluoroethyl thioethers from aromatic amines and tetramethylammonium pentafluoroethylthiolate.
Highlights
View Article OnlineConvenient synthesis of pentafluoroethyl thioethers via catalytic Sandmeyer reaction
Aromatic and heteroaromatic diazonium salts were smoothly converted into the corresponding pentafluoroethyl thioethers by reaction with Me4NSC2F5 in the presence of catalytic amounts of elemental copper
We have demonstrated that a Sandmeyer-thiocyanation followed by a Langlois-type nucleophilic CN/CF3- or CF2Hexchange allows the convenient synthesis of fluoroalkylthioethers.8f,9 For laboratory-scale applications, the use of preformed reagents such asCuSCF3,10 AgSCF3 5a and Me4NSCF3 are more convenient
Summary
Convenient synthesis of pentafluoroethyl thioethers via catalytic Sandmeyer reaction. Aromatic and heteroaromatic diazonium salts were smoothly converted into the corresponding pentafluoroethyl thioethers by reaction with Me4NSC2F5 in the presence of catalytic amounts of elemental copper. This Sandmeyer-type reaction proceeds at room temperature under mild conditions and is applicable to a wide range of functionalised molecules. A generally applicable, regiospecific method for the introduction of SC2F5 groups within a single step, based on widely available substrates and an inexpensive fluoroalkylation reagent, would be highly desirable. We approached this challenge by investigating Sandmeyertype pentafluoroethylthiolations (Scheme 1). In order to probe the viability of our approach, we treated 4-methoxybenzenediazonium tetrafluoroborate with Me4NSC2F5 in the presence of 10 mol% CuSCN in acetonitrile at room temperature, conditions previously optimised for
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