Use of mixed Li/K metal TMP amide (LiNK chemistry) for the synthesis of [2.2]metacyclophanes
2011

Synthesis of [2.2]metacyclophanes using LiNK chemistry

publication Evidence: moderate

Author Information

Author(s): Blangetti Marco, Fleming Patricia, O'Shea Donal F, Snieckus Victor

Primary Institution: University College Dublin

Hypothesis

Can a new two-step approach using LiNK metalation conditions effectively synthesize [2.2]metacyclophanes from substituted m-xylenes?

Conclusion

The study presents a new two-step method for synthesizing [2.2]metacyclophanes that is simpler and more efficient than previous methods.

Supporting Evidence

  • The method allows for the synthesis of potentially useful planar chiral derivatives.
  • The approach compares favorably with previously reported methods.
  • The study demonstrated good to excellent yields for the targeted homo-dimer products.

Takeaway

Scientists found a new way to make special chemical structures called [2.2]metacyclophanes using a simpler method that works better than older ones.

Methodology

The study used a two-step process involving selective benzylic metalation and oxidative C–C bond formation under LiNK metalation conditions.

Limitations

The study does not address the scalability of the method or potential side reactions in complex substrates.

Digital Object Identifier (DOI)

10.3762/bjoc.7.145

Want to read the original?

Access the complete publication on the publisher's website

View Original Publication