Modification of fluorene and fluorenone core via C-H functionalization
Shefali Banga1, Srinivasarao Arulananda Babu1
1Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali, Knowledge City, Sector 81, SAS Nagar, Mohali, Manauli P.O., Punjab, 140306, India. sababu@iisermohali.ac.in.
This study introduces a new C-H functionalization strategy to create diverse libraries of modified fluorenes and fluorenones. These versatile compounds have applications in materials science and medicinal chemistry.
Area of Science:
- Organic Chemistry
- Materials Science
- Medicinal Chemistry
Background:
- Fluorene and fluorenone cores are essential building blocks in materials science.
- These motifs are also found in various bioactive compounds.
- Expanding the library of functionalized fluorenes/fluorenones is crucial for further applications.
Purpose of the Study:
- To develop a C(sp2)-H and C(sp3)-H functionalization strategy for fluorene and fluorenone cores.
- To synthesize diverse libraries of modified fluorenes and fluorenones.
- To explore new synthetic routes for advanced fluorene-based materials.
Main Methods:
- Direct C-H arylation, alkylation, benzylation, alkoxylation, and annulation reactions on fluorene and fluorenone.
- C-H arylation of aryl or alkyl carboxamides using iodofluorenes or iodofluorenones.
- Synthesis of various functionalized fluorenes, fluorenones, and their coupled structures.
Main Results:
- Successfully modified fluorene and fluorenone cores using C-H functionalization.
- Generated libraries of C(1), C(2), C(3), and C(4) functionalized fluorenes and fluorenones.
- Synthesized fluorene-fluorenone, fluorene-carbazole couples, and π-extended bis fluorenes, including enantioenriched forms.
Conclusions:
- The developed C(sp2)-H and C(sp3)-H functionalization strategy effectively augments the fluorene and fluorenone library.
- This work provides a versatile platform for accessing novel fluorene-based compounds.
- The synthesized compounds hold potential for advanced materials and medicinal chemistry applications.
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