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Title
Japanese: 
English:2,3,5,6,8,9-Hexabromosumanene: Synthesis and Its Application to Suzuki-Miyaura Cross-Coupling 
Author
Japanese: Hideaki Toda, Yumi Yakiyama, 庄子良晃, 石割文崇, 福島孝典, 櫻井英博.  
English: Hideaki Toda, Yumi Yakiyama, Yoshiaki Shoji, Fumitaka Ishiwari, Takanori Fukushima, Hidehiro Sakurai.  
Language English 
Journal/Book name
Japanese: 
English:Chemistry Letters 
Volume, Number, Page Vol. 46    No. 9    Page 1368-1371
Published date June 2017 
Publisher
Japanese: 
English: 
Conference name
Japanese: 
English: 
Conference site
Japanese: 
English: 
Official URL http://www.journal.csj.jp/doi/abs/10.1246/cl.170566
 
DOI https://doi.org/10.1246/cl.170566
Abstract 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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