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Facile and Diverse Synthesis of Benzo[ b ]fluorenone Derivatives through a Copper/Selectfluor‐Catalyzed Tandem Annulation of 1,6‐Enynes
Author(s) -
Zhang Jian,
Zhang Haifeng,
Shi Dongdong,
Jin Hongwei,
Liu Yunkui
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600982
Subject(s) - annulation , chemistry , tandem , fluorenone , selectfluor , bond cleavage , cleavage (geology) , trimethylsilyl , medicinal chemistry , aryl , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , fluorene , materials science , polymer , geotechnical engineering , alkyl , fracture (geology) , engineering , composite material
A facile synthesis of a diverse array of benzo[ b ]fluorenone derivatives has been developed. The method involves a Cu 0 /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.