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Boronate Ester Bullvalenes

preprint
submitted on 22.11.2019 and posted on 29.11.2019 by Harshal Patel, Thanh Huyen Tran, Christopher Sumby, Lukáš Pašteka, Thomas Fallon

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.

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

History

Email Address of Submitting Author

thomas.fallon@adelaide.edu.au

Institution

The University of Adelaide

Country

Australia

ORCID For Submitting Author

0000-0002-6495-5282

Declaration of Conflict of Interest

none

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in Journal of the American Chemical Society

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