Rapid access to dibenzohelicenes and their functionalized derivatives
Andrej Jančařík1, Jiří Rybáček, Kevin Cocq
1Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6 (Czech Republic).
Angewandte Chemie (International Ed. in English)
|August 13, 2013
Summary
Researchers developed a simple, non-photochemical method for synthesizing dibenzohelicenes. This approach offers better helicity control, making these complex molecules more accessible for practical applications.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Helicenes are chiral aromatic compounds with unique three-dimensional structures.
- Dibenzohelicenes offer enhanced stability and tunable properties compared to parent helicenes.
- Accessing functionalized dibenzohelicenes is crucial for exploring their applications.
Purpose of the Study:
- To develop a straightforward and efficient synthetic route to dibenzo[5]-, dibenzo[6]-, and dibenzo[7]helicenes.
- To demonstrate the utility of this method for creating functionalized derivatives.
- To highlight the advantages of this approach for controlling helicity.
Main Methods:
- Sonogashira coupling
- Suzuki-Miyaura coupling
- Desilylation
- [2+2+2] alkyne cycloisomerization
Main Results:
- Successful synthesis of dibenzo[5]-, dibenzo[6]-, and dibenzo[7]helicenes.
- Demonstrated feasibility of synthesizing functionalized derivatives.
- Established a non-photochemical route with potential for helicity control.
Conclusions:
- The developed synthetic strategy provides easy access to dibenzohelicenes and their derivatives.
- This method is advantageous over parent helicenes due to its simplicity and helicity control.
- The findings facilitate practical applications of dibenzohelicenes.
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