Homocoupling of aryl halides in flow: Space integration of lithiation and FeCl3 promoted homocoupling
2011

Fast Homocoupling of Aryl Halides in Flow Systems

publication Evidence: high

Author Information

Author(s): Nagaki Aiichiro, Uesugi Yuki, Tomida Yutaka, Yoshida Jun-ichi, Kirschning Andreas

Primary Institution: Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University

Hypothesis

Can the integration of lithiation and FeCl3 promoted homocoupling in a flow microreactor enhance the efficiency of biaryl synthesis?

Conclusion

The use of FeCl3 enables rapid oxidative homocoupling of aryllithiums, integrating it with the halogen–lithium exchange of aryl halides.

Supporting Evidence

  • The integrated flow microreactor system allows for the rapid generation and reaction of unstable aryllithium intermediates.
  • High yields of homocoupling products were achieved even at low temperatures.
  • The method enhances the synthetic utility of aryllithium compounds.

Takeaway

This study shows that we can quickly make complex molecules using a special setup that combines two chemical reactions in one go.

Methodology

The study utilized a flow microreactor system to integrate the generation of aryllithiums and their subsequent homocoupling with FeCl3.

Digital Object Identifier (DOI)

10.3762/bjoc.7.122

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