Akhmetov Vladimir, Feofanov Mikhail, Ruppenstein Cordula, Lange Josefine, Sharapa Dmitry, Krstić Marjan, Hampel Frank, Kataev Evgeny A, Amsharov Konstantin
Martin-Luther-Universität Halle-Wittenberg, Institute of Chemistry, Organic Chemistry, Kurt-Mothes-Strasse 2, 06120, Halle, Germany.
Karlsruhe Institute of Technology, Institute of Catalysis Research and Technology, Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany.
Chemistry. 2022 Jun 1;28(31):e202200584. doi: 10.1002/chem.202200584. Epub 2022 Apr 26.
We have discovered a dual (i. e., soft and hard) Lewis acidity of alumina that enables rapid one-pot π-extension through the activation of terminal alkynes followed by C-F activation. The tandem reaction introduces an acenaphthene fragment - an essential moiety of geodesic polyarenes. This reaction provides quick access to elusive non-alternant polyarenes such as π-extended buckybowls and helicenes through three-point annulation of the 1-(2-ethynyl-6-fluorophenyl)naphthalene moiety. The versatility of the developed method was demonstrated by the synthesis of unprecedented structural fragments of elusive geodesic graphene nanoribbons.
我们发现氧化铝具有双重（即软硬兼具）路易斯酸性，能够通过活化末端炔烃随后进行碳氟活化实现快速一锅法π-扩展。该串联反应引入了苊片段——测地线多芳烃的一个关键部分。此反应通过1-(2-乙炔基-6-氟苯基)萘部分的三点环化，可快速获得难以捉摸的非交替多芳烃，如π-扩展的巴基碗和螺旋烯。通过合成难以捉摸的测地线石墨烯纳米带的前所未有的结构片段，证明了所开发方法的通用性。
