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An expeditious, high-yielding synthesis of rare α-fluoroepoxides and α-fluoroaziridines through the addition of the unkown fluoroiodomethyllithium (LiCHIF)-formed via deprotonation the commercially available fluoroiodomethane with a lithium amide base-to carbonyl-like compounds is documented. The ring-closure reactions, leading to α-fluorinated three-membered heterocycles, rely on the diversely reactive C-I and C-F bonds. Excellent chemoselectivity was observed in the presence of highly sensitive functionalities-aldehyde, ketone, nitrile, alkene-which remained untouched during the homologation sequence.
PMID: 30600682 [PubMed - as supplied by publisher]