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Switching the Statistical C 3 / C 1 Ratio in the Threefold Aromatic Substitution of Tribenzotriquinacenes towards the C 3 Isomer
Author(s) -
Wagner Philippe,
Rominger Frank,
Mastalerz Michael
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201806332
Subject(s) - supramolecular chemistry , chemistry , electrophilic substitution , borylation , substitution (logic) , block (permutation group theory) , molecule , electrophile , stereochemistry , medicinal chemistry , organic chemistry , combinatorics , computer science , catalysis , mathematics , alkyl , aryl , programming language
Abstract Tribenzotriquinacene (TBTQ) is a bowl‐shaped molecule that has been widely used as a molecular building block in supramolecular and materials chemistry. Especially C 3 ‐symmetric threefold‐substituted TBTQs are interesting for these purposes. Until now a general and selective synthetic approach to those C 3 ‐symmetric products was lacking, mainly because the typically used electrophilic aromatic substitution reactions of the parent TBTQ hydrocarbons produce predominantly the C 1 isomer over the C 3 isomer (3:1 statistical ratio). Herein we introduce a threefold borylation of TBTQ with the C 3 isomer as the main product (2.6:1 C 3 / C 1 ratio). The borylated TBTQ can be converted in good yields into other C 3 ‐symmetric TBTQs, thus allowing straightforward synthetic access to new building blocks for supramolecular and materials chemistry.