Synthesis of Acenaphthylene-Fused Heteroarenes and Polyoxygenated Benzo[j]fluoranthenes
Author Information
Author(s): Yence Merve, Ahmadli Dilgam, Surmeli Damla, Karacaoğlu Umut Mert, Pal Sujit, Türkmen Yunus Emre
Primary Institution: Bilkent University
Hypothesis
Can a Pd-catalyzed reaction cascade effectively synthesize acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes?
Conclusion
The study successfully synthesized various acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes using a Pd-catalyzed reaction cascade.
Supporting Evidence
- The method achieved good to high yields (45–90%) for various heterocycles.
- The study demonstrated the effectiveness of using both boronic acids and esters in the synthesis.
- The synthesis of tetramethoxybenzo[j]fluoranthene represents a formal total synthesis of the fungal natural product bulgarein.
Takeaway
The researchers found a way to make new chemical compounds that could be useful in medicines and materials by combining different chemicals in a smart way.
Methodology
The study utilized a Pd-catalyzed reaction cascade involving Suzuki–Miyaura cross-coupling followed by intramolecular C–H arylation.
Limitations
The synthesis of benzo[j]fluoranthene derivatives with free -OH groups may be challenging due to the protection of oxygen atoms.
Digital Object Identifier (DOI)
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