Abstract
Fluorenes and methylene-bridged polyarenes were easily and efficiently synthesized from haloarenes (or aryl triflates) and diarylethynes by a one-pot, two-step procedure. This protocol involves the palladium-catalyzed cycloisomerization and a subsequent base-mediated retro-aldol condensation. A major advantage is that the starting materials need not have ortho functional groups to complete the annulation. The backbone of the designed products was enlarged using dihaloarenes, highly π-conjugated haloarenes, or diarylalkynes. The mechanism of the formation of benzo[a]fluorene was investigated. The bowl-shaped structure of methylene-bridged indenocorannulene was verified by X-ray crystallography. The photophysical and electrochemical properties of the products thus prepared were investigated.
Recommended Citation
C. Lee et al., "Palladium-Catalyzed Reaction of Haloarenes with Diarylethynes: Synthesis, Structural Analysis, and Properties of Methylene-Bridged Arenes," The Journal of Organic Chemistry, vol. 80, article no. 10446, American Chemical Society, Jan 2015.
The definitive version is available at https://doi.org/10.1021/acs.joc.5b02111
Department(s)
Chemistry
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2025 American Chemical Society, all rights reserved
Publication Date
2015
