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 |
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Rok vydání: | 2019 |
Předmět: |
chemistry.chemical_classification
Ketone Lithium amide Nitrile 010405 organic chemistry Organic Chemistry Sequence (biology) 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Highly sensitive chemistry.chemical_compound Deprotonation chemistry Physical and Theoretical Chemistry Chemoselectivity |
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 |
Externí odkaz: |
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