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.

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

Colella, Marco
Membro del Collaboration Group
;
Tota, Arianna
Membro del Collaboration Group
;
Degennaro, Leonardo
Supervision
;
Luisi, Renzo
Supervision
;
2019

Abstract

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.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11586/225892
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