Consecutive HDDA and TDDA reactions of silicon-tethered tetraynes for the synthesis of dibenzosilole-fused polycyclic compounds and their unique reactivity

Akihito Mitake; Rikako Nagai; Ayato Sekine; Hideaki Takano; Natsuhiko Sugimura; Kyalo Stephen Kanyiva; Takanori Shibata

doi:10.1039/c9sc00960d

Consecutive HDDA and TDDA reactions of silicon-tethered tetraynes for the synthesis of dibenzosilole-fused polycyclic compounds and their unique reactivity

Chem Sci. 2019 May 30;10(27):6715-6720. doi: 10.1039/c9sc00960d. eCollection 2019 Jul 21.

Authors

Akihito Mitake¹, Rikako Nagai¹, Ayato Sekine¹, Hideaki Takano¹, Natsuhiko Sugimura², Kyalo Stephen Kanyiva³, Takanori Shibata¹

Affiliations

¹ Department of Chemistry and Biochemistry , School of Advanced Science and Engineering , Waseda University , Shinjuku , Tokyo 169-8555 , Japan . Email: tshibata@waseda.jp.
² Materials Characterization Central Laboratory , School of Advanced Science and Engineering , Waseda University , Shinjuku , Tokyo 169-8555 , Japan.
³ Global Center for Science and Engineering , School of Advanced Science and Engineering , Waseda University , Shinjuku , Tokyo 169-8555 , Japan.

Abstract

Silicon-tethered tetraynes possessing a 1,3-diyne moiety underwent consecutive hexadehydro- and tetradehydro-Diels-Alder reactions to give a series of fused polycyclic aromatic compounds containing a dibenzosilole skeleton. The benzene ring in the product acted as a 1,3-diene and reacted with the active alkyne as well as oxygen to provide [4 + 2] cycloadducts.