Switching the statistical C3/C1 ratio in the threefold aromatic substitution of tribenzotriquinacenes towards the C3 isomer
Tribenzotriquinacene (TBTQ) is a bowl-shaped molecule that has been widely used as a molecular building block in supramolecular and materials chemistry. Especially C3-symmetric threefold-substituted TBTQs are interesting for these purposes. Until now a general and selective synthetic approach to tho...
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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
25 June 2018
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| In: |
Angewandte Chemie. International edition
Year: 2018, Volume: 57, Issue: 35, Pages: 11321-11324 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201806332 |
| Online Access: | Verlag, Volltext: https://doi.org/10.1002/anie.201806332 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201806332 
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| Author Notes: | Philippe Wagner, Frank Rominger, Michael Mastalerz |
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| 520 | |a Tribenzotriquinacene (TBTQ) is a bowl-shaped molecule that has been widely used as a molecular building block in supramolecular and materials chemistry. Especially C3-symmetric threefold-substituted TBTQs are interesting for these purposes. Until now a general and selective synthetic approach to those C3-symmetric products was lacking, mainly because the typically used electrophilic aromatic substitution reactions of the parent TBTQ hydrocarbons produce predominantly the C1 isomer over the C3 isomer (3:1 statistical ratio). Herein we introduce a threefold borylation of TBTQ with the C3 isomer as the main product (2.6:1 C3/C1 ratio). The borylated TBTQ can be converted in good yields into other C3-symmetric TBTQs, thus allowing straightforward synthetic access to new building blocks for supramolecular and materials chemistry. | ||
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| 650 | 4 | |a C−H activation | |
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| 650 | 4 | |a regioselectivity | |
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