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

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.



Titolo: Modular and Chemoselective Strategy for the Direct Access to α-Fluoroepoxides and Aziridines via the Addition of Fluoroiodomethyllithium to Carbonyl-Like Compounds
Autori: 
MONTICELLI, SERENA
COLELLA, MARCO
TOTA, ARIANNA
DEGENNARO, LEONARDO
LUISI, Renzo
mostra contributor esterni 
Data di pubblicazione: 2019
Rivista: 
ORGANIC LETTERS  
Handle: http://hdl.handle.net/11586/225892
Appare nelle tipologie:1.1 Articolo in rivista

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