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Boronate Ester Bullvalenes.

Harshal D Patel1, Thanh-Huyen Tran1, Christopher J Sumby1

  • 1Department of Chemistry , The University of Adelaide , Adelaide 5005 , SA , Australia.

Journal of the American Chemical Society
|February 12, 2020
PubMed
Summary
This summary is machine-generated.

New methods allow easy synthesis of boronate ester bullvalenes. This enables late-stage diversification via Suzuki coupling, creating various substituted bullvalenes with controlled isomer distribution.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Bullvalenes are highly fluxional molecules with dynamic structures.
  • Access to substituted bullvalenes is crucial for studying their unique properties.

Purpose of the Study:

  • To develop efficient synthetic routes to boronate ester bullvalenes.
  • To enable late-stage diversification of bullvalene scaffolds.
  • To investigate the factors governing isomer distribution in bullvalenes.

Main Methods:

  • Development of a 2-4 step synthetic procedure for boronate ester bullvalenes.
  • Application of Suzuki cross-coupling reactions for diversification.
  • Utilisation of a linchpin strategy for preprogrammed substituent installation.
  • Analysis of solution phase isomer distributions and single-crystal X-ray structures.

Main Results:

  • Boronate ester bullvalenes are readily synthesized.
  • Mono-, di-, and trisubstituted bullvalenes are accessible through Suzuki coupling.
  • A linchpin strategy allows for the controlled introduction of two distinct substituents.
  • Isomer preference in the crystal lattice is determined by general shape selectivity.

Conclusions:

  • Efficient synthetic access to functionalized bullvalenes has been established.
  • Late-stage diversification strategies provide versatile routes to complex bullvalene derivatives.
  • Shape selectivity governs the observed isomer distributions in the solid state.