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,...

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Veröffentlicht in:Journal of organic chemistry 2021-08, Vol.86 (15), p.10043-10054
Hauptverfasser: Lv, Yunhe, Pu, Weiya, Zhu, Xueli, Chen, Chen, Wang, Shanshan
Format: Artikel
Sprache:eng
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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