Journal Article 2,3,5,6,8,9-Hexabromosumanene: Synthesis and Its Application to Suzuki-Miyaura Cross-Coupling

Toda, Hideaki  ,  Yakiyama, Yumi  ,  庄子, 良晃  ,  Shoji, Yoshiaki  ,  石割, 文崇  ,  Ishiwari, Fumitaka  ,  福島, 孝典  ,  Fukushima, Takanori  ,  櫻井, 英博  ,  Sakurai, Hidehiro

2,3,5,6,8,9-hexabromosumanene (2) with Br groups at all the peripheral aromatic carbons was successfully synthesized. Single-crystal X-ray structural analysis of 2 revealed the formation of a one-dimensional columnar structure in the solid state, where the molecules overlapped in an eclipsed manner. The Suzuki-Miyaura cross-coupling of 2 and various arylboronic acids gave hexaarylsumanene derivatives (3a–3h) in good-to-moderate yields. The NMR spectroscopic analysis and theoretical calculations of 2 and hexaphenylsumanene (3a) revealed that the six peripheral functional groups do not significantly affect the original bowl structure and bowl-to-bowl inversion behavior of sumanene.

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