Copper-Catalyzed 1,1-Alkylmonofluoroalkylation of Terminal Alkynes with Diazo Compounds and 2‑Fluoro-1,3-dicarbonyl Compounds: Access toward (E)‑β-Monofluoroalkyl-β,γ-unsaturated Esters or Ketones
An efficient copper-catalyzed three-component 1,1-alkylmonofluoroalkylation of terminal alkynes, diazo compounds, and 2-fluoro-1,3-dicarbonyl compounds for the synthesis of (E)-β-monofluoroalkyl-β,γ-unsaturated esters or ketones has been developed. The methodology features a broad substrate scope,...
Gespeichert in:
Veröffentlicht in: | Journal of organic chemistry 2021-08, Vol.86 (15), p.10043-10054 |
---|---|
Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
Zusammenfassung: | An efficient copper-catalyzed three-component 1,1-alkylmonofluoroalkylation of terminal alkynes, diazo compounds, and 2-fluoro-1,3-dicarbonyl compounds for the synthesis of (E)-β-monofluoroalkyl-β,γ-unsaturated esters or ketones has been developed. The methodology features a broad substrate scope, an inexpensive and easily available catalytic system, and excellent selectivity with good yields. The mechanism of the tandem Cu-catalyzed cross-coupling and nucleophilic addition of allenes has been investigated. |
---|---|
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.1c00789 |