Development of a Trifluoropropynylation Reagent

Access to both alkyne and fluorine containing building blocks are of broad interest to small molecule synthesis. Whilst many reagents have been developed to install various fluorinated fragments into molecules there has not been a straightforward to use reagent for the installation of trifluoropropynyl functionality. This has led to the trifluoropropynyl fragment (CCCF3) being underexplored as a functional group and under exploited as a synthetic intermediate.

Recent work in our group has revealed that the commodity refrigerant gas (HFO-1234yf) can be utilised a source of trifluoromethyl alkynes. Therefore, this project will utilise this knowledge to access new reagents capable of delivering the CCCF3 fragment in both nucleophilic and electrophilic manners. The chemistries will be used to access a variety of fluorinated small molecules, and the range of compatible reactions explored.