Switching the statistical C3/C1 ratio in the threefold aromatic substitution of tribenzotriquinacenes towards the C3 isomer

• Verfasst von: Wagner, Philippe [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Mastalerz, Michael [VerfasserIn]
• Titel: Switching the statistical C3/C1 ratio in the threefold aromatic substitution of tribenzotriquinacenes towards the C3 isomer
• Verf.angabe: Philippe Wagner, Frank Rominger, Michael Mastalerz
• E-Jahr: 2018
• Jahr: 25 June 2018
• Umfang: 4 S.
• Fussnoten: Im Titel ist "3" und "1" tiefgestellt ; Gesehen am 16.04.2019
• Titel Quelle: Enthalten in: Angewandte Chemie / International edition
• Ort Quelle: Weinheim : Wiley-VCH, 1962
• Jahr Quelle: 2018
• Band/Heft Quelle: 57(2018), 35, Seite 11321-11324
• ISSN Quelle: 1521-3773
• DOI: doi:10.1002/anie.201806332
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: borylation
• Sach-SW: C−H activation
• Sach-SW: iridium
• Sach-SW: regioselectivity
• Sach-SW: tribenzotriquinacenes
• K10plus-PPN: 1663288127

Abstract

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.