Modular and Chemoselective Strategy for the Direct Access to α-Fluoroepoxides and Aziridines via the Addition of Fluoroiodomethyllithium to Carbonyl-Like Compounds

Autor: Thierry Langer, Wolfgang Holzer, Arianna Tota, Veronica Pillari, Leonardo Degennaro, Renzo Luisi, Marco Colella, Serena Monticelli, Vittorio Pace
Rok vydání: 2019
Předmět:
Zdroj: Organic letters. 21(2)
ISSN: 1523-7052
Popis: 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.
Databáze: OpenAIRE
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