In this paper, the straightforward preparation of a range of functionalized trithiocarbonates as RAFT chain transfer agents (CTAs) is presented. The crucial step in the one-pot, three-step reaction sequence is the aminolysis of a thiolactone precursor as it introduces the desired functional handle (double bond, hydroxyl, furan, protected amine, ...) and generates the corresponding thiol in situ, facilitating further elaboration of the CTA. Furthermore, the newly synthesized trithiocarbonates were positively evaluated as mediators in the RAFT polymerization of styrene, isobornyl acrylate, and N-isopropylacrylamide, while the presence of the end groups in the heterotelechic polymers was confirmed by NMR and UV-vis analysis.