Copper-catalyzed ring-opening trifluoromethyl and sulfur trifluoromethylation of cyclopropanol
Purdue University Professor Dai Mingkai, Yong Li, Zhishi Ye and other coworkers for the first time realized copper-catalyzed cyclopropyl trifluoromethyl and sulfur trifluoromethyl of cyclopropanol ring opening reaction: The β-trifluoromethyl and sulfur trifluoromethylcarbonyl compounds is rapidly synthesized by using a readily available cyclopropanol as a substrate, a monovalent copper catalyst and the corresponding trifluoromethyl or sulfur trifluoromethyl reagent. The reaction conditions are mild and the functional group tolerance is good. The conjugate addition of α,β-unsaturated carbonyl compounds by nucleophilic trifluoromethyl reagents or thiotrifluoromethyl reagents is difficult, and this methodology cleverly exploits the polarity reversal strategy to achieve efficient construction of β- trifluoromethyl and sulfur trifluoromethyl carbonyl compounds. Subsequently, the author applied the methodology to prepare the drug LY2409021 which is during clinical trials quickly and efficiently.
The result of this research is published in "Org. Lett."