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Facile and Diverse Synthesis of Benzo[ b]fluorenone Derivatives through a Copper/Selectfluor-Catalyzed Tandem Annulation of 1,6-Enynes.
- Source :
- European Journal of Organic Chemistry; Nov2016, Vol. 2016 Issue 33, p5545-5558, 14p
- Publication Year :
- 2016
-
Abstract
- A facile synthesis of a diverse array of benzo[ b]fluorenone derivatives has been developed. The method involves a Cu<superscript>0</superscript>/Selectfluor-catalyzed tandem annulation of 1,6-enynes, which takes place under mild reaction conditions. For tert-butylethynyl-substituted 1,6-enynes, the major reaction pathway was a tandem annulation/C-C-bond-cleavage/fluorination process leading to fluorinated benzo[ b]fluorenones as the major products; tert-butyl-substituted benzo[ b]fluorenones were obtained as the minor products. For arylethynyl-substituted 1,6-enynes, the substrates underwent tandem annulations to give 5-aryl-substituted benzo[ b]fluorenones in moderate to excellent yields. For (trimethylsilyl)ethynyl-substituted 1,6-enynes, the reaction involved a tandem annulation/C-Si-bond-cleavage process to deliver 11 H-benzo[ b]fluoren-11-ones in moderate yields. [ABSTRACT FROM AUTHOR]
- Subjects :
- SCISSION (Chemistry)
CHEMICAL reactions
FLUORENONE
FLUOROQUINOLONES
ANNULATION
Subjects
Details
- Language :
- English
- ISSN :
- 1434193X
- Volume :
- 2016
- Issue :
- 33
- Database :
- Complementary Index
- Journal :
- European Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 119575286
- Full Text :
- https://doi.org/10.1002/ejoc.201600982