In summary, a synthetic method has been developed for the defluoroalkylation of HCF3. Reaction with silyl substituted organolithiums occurs with a 2:1 stoichiometry, extending the carbon chain and creating a new fluoroalkene functional group. Scale-up was achieved using a continuous flow process. The products could be employed in a stereospecific fluoroethenylation of electrophiles, allowing direct access to tri-substituted fluoroalkenes -useful bioisosteres for amide groups. Our study demonstrates an approach to repurpose HCF3 through creation of bench-stable and storable reagents using flow methodology. While these reagents conserve the valuable carbon and fluorine content from HCF3, they do not contain CF3 groups and hence may contribute to sustainable approaches to repurpose trifluoromethane.