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Towards macrocyclic frustrated Lewis pairs.

Jason Yeung1, Matthias Becker1, Douglas W Stephan1

  • 1Department of Chemistry, University of Toronto, Toronto, 80 St George Street, Ontario M5S 3H6, Canada. dstephan@chem.utoronto.ca.

Dalton Transactions (Cambridge, England : 2003)
|July 6, 2022
PubMed
Summary
This summary is machine-generated.

New macrocycles, with and without boron-nitrogen bonds, were synthesized. These macrocycles react with B(C6F5)3 but not small molecules, guiding future designs of macrocyclic frustrated Lewis pairs for multi-electron reactions.

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Area of Science:

  • Organometallic Chemistry
  • Supramolecular Chemistry
  • Boron Chemistry

Background:

  • Macrocyclic compounds are crucial in host-guest chemistry and catalysis.
  • Frustrated Lewis pairs (FLPs) are reactive species capable of small molecule activation.
  • Designing novel macrocyclic FLPs can unlock new reactivity for challenging transformations.

Purpose of the Study:

  • To synthesize and characterize novel macrocycles containing boron.
  • To investigate the reactivity of these macrocycles with Lewis acids and small molecules.
  • To establish a foundation for the development of macrocyclic FLPs for multi-electron reactions.

Main Methods:

  • Synthesis of macrocycles via the reaction of C6F5BH2·SMe2 or MesBH2 with 2,6-pyridinedimethanol derivatives.
  • Characterization of synthesized macrocycles using standard spectroscopic techniques.
  • Reactivity studies involving B(C6F5)3 and various small molecules.

Main Results:

  • Successfully prepared macrocycles featuring both B-N bonds and those without.
  • Observed that both classes of macrocycles readily react with the strong Lewis acid B(C6F5)3.
  • Demonstrated the unreactivity of these macrocycles towards common small molecules, indicating Lewis pair frustration.

Conclusions:

  • The synthesized macrocycles exhibit unique reactivity profiles, reacting with strong Lewis acids but not small molecules.
  • These findings are pivotal for the rational design of next-generation macrocyclic frustrated Lewis pairs.
  • The developed macrocycles offer a promising platform for exploring multi-electron reaction chemistry.