Boronate Ester Bullvalenes

29 November 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Boronate ester bullvalenes are now accessible in two to four operationally simple steps. This unlocks late-stage diversification through Suzuki cross-coupling reactions to give mono-, di-, and tri-substituted bullvalenes. Moreover, a linchpin strategy enables pre-programmed installation of two different substituents. Analysis of solution phase isomer distributions and single crystal X-ray structures reveals that isomer preference in the crystal lattice is due to general shape selectivity.

Keywords

Bullvalene
[6+2] Cycloaddition
Di-pi-methane Rearrangement
Suzuki Cross-Coupling Reactions
Shape Selectivity
Fluxional Molecules

Supplementary materials

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boronate ester bullvalenes chemrxiv SI sub
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