1647063-44-2Relevant academic research and scientific papers
Synthesis of allylic and propargylic trifluoromethyl thioethers by copper(i)-catalyzed trifluoromethylthiolation of allylic bromides and propargylic chlorides
Rong, Mingguang,Li, Dongzhe,Huang, Ronglu,Huang, Yangjie,Han, Xiaoyan,Weng, Zhiqiang
, p. 5010 - 5016 (2014/08/18)
An efficient method is reported for the copper(I)-catalyzed trifluoromethylthiolation of allylic bromides by using elemental sulfur and CF3SiMe3. This rate of this transformation was significantly accelerated in the presence of 18-crown-6, and the reaction afforded the desired products in moderate to excellent yields with high stereo- and regioselectivity. This method can tolerate a number of functional groups and provides facile access to a variety of allylic trifluoromethyl thioethers. The copper(I)-catalyzed trifluoromethylthiolation of propargylic chlorides was also investigated. A plausible mechanism that involves an allylcopper(III) intermediate is proposed.
