Abstract
A novel copper-catalyzed thioetherification reaction has been developed to afford benzyl thioethers in moderate to excellent yields. Under the mild and easy-to-operate conditions, a variety of thioethers are efficiently prepared from readily available benzyl alcohols (primary, secondary, and tertiary) and thiols in the presence of Cu(OTf)2 as the Lewis acid catalysis. This C–S bond formation protocol furnishes exceptional chemoselectivity, and the preliminary mechanism studies show that the reaction should proceed through a Lewis-acid-mediated SN1-type nucleophilic attack of the carbocations formed in situ.
Highlights
Sulfur compounds o en show different biological activities and have important application value in the pharmaceutical industry.[1]
We explored a process for thioetheri cation of benzyl alcohols with thiols catalyzed by a Cucomplex with intriguing results (Scheme 1C)
A er an additional screening of the reaction conditions revealed that the use of Cu(OTf)[2] (8 mol%) in DCE at an air atmosphere of 70 C that were applicable for the amination of benzyl alcohols with benzenamine (Fig. 2)
Summary
Sulfur compounds o en show different biological activities and have important application value in the pharmaceutical industry.[1]. We explored a process for thioetheri cation of benzyl alcohols with thiols catalyzed by a Cucomplex with intriguing results (Scheme 1C). We initiated our investigation by exploring the thioetheri cation of 2-phenylpropan-2-ol 1 with 4- uorobenzenethiol 2 as the model substrates (Table 1).[21] An extensive screening of the reaction parameters revealed that the use of Cu(OTf)[2] (3 mol%) in DCM (dichloromethane) at an air atmosphere of 25 C delivered benzyl sul de product 3 in 96% yield (entry 1).
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
