Synonyms:Nonafluorobutansulfonsaeure-trifluormethylester
The study introduces trifluoromethyl nonaflate (TFNf) as a novel and practical trifluoromethoxylating reagent. TFNf is an odorless liquid with a boiling point of 87-89°C, making it easy to handle and thermally stable. It can be prepared in large scale through a safe and efficient process involving the thermolysis of nonaflate 3 or its tetrafluoro analog 3c. The nonaflyl part of TFNf can be easily recovered and recycled after use. The study demonstrates TFNf's high synthetic potential through its application in the regio- and stereoselective hydro(halo)trifluoromethoxylation of various alkyne derivatives, including chloroalkynes, alkynyl esters, and alkynyl sulfones. The reactions are characterized by wide functional group compatibility, good yields, and scalability to gram-scale synthesis. TFNf, in conjunction with AgF, activates the alkyne triple bond and facilitates the formation of trifluoromethoxylated alkenes. The study also explores the use of TFNf in other trifluoromethoxylation reactions, such as nucleophilic substitution of alkyl (pseudo)halides and one-pot trifluoromethoxylation of primary/secondary alcohols via triflates, further highlighting its versatility and potential for broader applications in pharmaceutical and agrochemical research and development.
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