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Boronate Ester Bullvalenes

29 November 2019, Version 1
Working Paper
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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Now Published

Boronate Ester Bullvalenes [opens in a new tab]
Harshal D. Patel, Thanh-Huyen Tran, Christopher J. Sumby, Lukáš F. Pašteka, Thomas Fallon journal article
Journal of the American Chemical Society , Volume 142, Issue 8
Online publication date: Feb 11, 2020

Version History

Nov 29, 2019 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.10732838.v1
D O I: 10.26434/chemrxiv.10732838.v1 [opens in a new tab]

Funding

Slovak Academy of Sciences, ITMS 26230120002
Marsden Fund, 15-MAU-154
Slovak Academy of Sciences, ITMS 26210120002
Slovak Research and Development Agency, APVV-15-0105
Scientific Grant Agency of the Slovak Republic, 1/0777/19
Australian Research Council, LE0989336

Author’s competing interest statement

none

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