Wagner Philippe, Rominger Frank, Mastalerz Michael
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Angew Chem Int Ed Engl. 2018 Aug 27;57(35):11321-11324. doi: 10.1002/anie.201806332. Epub 2018 Jul 26.
Tribenzotriquinacene (TBTQ) is a bowl-shaped molecule that has been widely used as a molecular building block in supramolecular and materials chemistry. Especially C -symmetric threefold-substituted TBTQs are interesting for these purposes. Until now a general and selective synthetic approach to those C -symmetric products was lacking, mainly because the typically used electrophilic aromatic substitution reactions of the parent TBTQ hydrocarbons produce predominantly the C isomer over the C isomer (3:1 statistical ratio). Herein we introduce a threefold borylation of TBTQ with the C isomer as the main product (2.6:1 C /C ratio). The borylated TBTQ can be converted in good yields into other C -symmetric TBTQs, thus allowing straightforward synthetic access to new building blocks for supramolecular and materials chemistry.
三棱并三蝶烯（TBTQ）是一种碗状分子，在超分子化学和材料化学中作为分子构建单元被广泛应用。特别是具有C对称性的三取代TBTQ在这些领域很有吸引力。到目前为止，还缺乏一种通用且选择性地合成这些具有C对称性产物的方法，主要是因为母体TBTQ烃类通常使用的亲电芳香取代反应主要生成C异构体而非C异构体（统计比例为3:1）。在此，我们介绍了一种TBTQ的三硼化反应，主要产物为具有C对称性的异构体（C /C比例为2.6:1）。硼化的TBTQ可以高收率转化为其他具有C对称性的TBTQ，从而为超分子化学和材料化学提供了直接合成新构建单元的途径。
