A facile and versatile approach to double N-heterohelicenes: tandem oxidative C-N couplings of N-Heteroacenes via cruciform dimers

Angewandte Chemie
Daisuke SakamakiShu Seki

Abstract

Novel double N-hetero[5]helicenes that are composed of two nitrogen-substituted heteropentacenes are synthesized by tandem oxidative CN couplings via the cruciform heteropentacene dimers. The developed method is very facile and enables the synthesis of a double helicene in only two steps from commercially available naphthalene derivatives. These double N-hetero[5]helicenes have larger torsion angles in the fjord regions than typical [5]helicenes, and optical/electrochemical measurements revealed a significant increase in the electronic communication between the two heteropentacene moieties of the double helicenes compared with their cruciform dimers. The optical resolution of one of the double helicenes was successfully carried out, and their stability towards racemization was remarkably higher than those of typical [5]helicenes. The synthetic strategy proposed in this paper should be versatile and widely applicable to the preparation of double helicenes from other N-containing π-conjugated planar molecules.

References

Jun 30, 2005·Journal of the American Chemical Society·Kouichi ShiraishiSuchada Rajca
Apr 2, 2009·Chemistry : a European Journal·Shaobin MiaoUwe H F Bunz
Nov 4, 2009·The Journal of Organic Chemistry·Gary J RichardsKatsuhiko Ariga
Oct 26, 2010·Chemical Communications : Chem Comm·Niksa KulisicAurelio Mateo-Alonso
Mar 31, 2011·Advanced Materials·Zhixiong LiangQian Miao
Nov 8, 2011·Advanced Materials·Zhixiong LiangQian Miao
Jul 26, 2012·Journal of the American Chemical Society·Jiye LuoQian Miao
Sep 12, 2012·Angewandte Chemie·Kiyohiko GotoHiroshi Shinokubo
Feb 20, 2013·Angewandte Chemie·Uwe H F BunzManuel Schaffroth
May 30, 2013·The Journal of Organic Chemistry·Xinming LiuHua Wang
Jul 5, 2013·Organic Letters·Xing FengTakehiko Yamato
Oct 15, 2013·Chemistry : a European Journal·Jens U EngelhartUwe H F Bunz
Mar 29, 2014·Journal of the American Chemical Society·Kyosuke NakamuraKen Tanaka
Mar 29, 2014·Chemistry : a European Journal·Sandeep MoreAurelio Mateo-Alonso
Oct 9, 2014·Journal of the American Chemical Society·Jens U EngelhartUwe H F Bunz
Oct 17, 2014·Angewandte Chemie·Sigma HashimotoTakuji Hatakeyama

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Citations

Apr 15, 2016·Journal of the American Chemical Society·Takazumi KatayamaTakuji Hatakeyama
Jul 5, 2016·Journal of the American Chemical Society·Xiao-Ye WangKlaus Müllen
Sep 23, 2016·Journal of the American Chemical Society·Xiao-Ye WangKlaus Müllen
Oct 16, 2015·Chemical Communications : Chem Comm·Daisuke SakamakiShu Seki
Feb 13, 2018·Chemistry, an Asian Journal·Changqing LiQian Miao
Jun 15, 2018·Angewandte Chemie·Cheng ZengZhaohui Wang
Jul 25, 2017·Chemistry : a European Journal·Koji YamamotoShuhei Higashibayashi
Aug 14, 2019·Angewandte Chemie·Xiaoyu GuoJiaobing Wang
Oct 21, 2016·Chemistry : a European Journal·Thomas BietNarcis Avarvari
Nov 24, 2020·Chemistry : a European Journal·Gaozhan XieUwe H F Bunz
Jan 12, 2021·Chemistry : a European Journal·Katsuki TanakaHideki Fujiwara
Apr 4, 2020·Journal of the American Chemical Society·Nathaniel J SchusterColin Nuckolls
Apr 10, 2021·Chemistry : a European Journal·Nozomi TeradaKyoko Nozaki
Jun 2, 2015·Journal of the American Chemical Society·Takao FujikawaKenichiro Itami
Jan 11, 2019·Journal of the American Chemical Society·Expédite Yen-PonDavide Audisio
Mar 15, 2018·Journal of the American Chemical Society·Yanpeng ZhuJiaobing Wang
Jul 12, 2019·Chemical Reviews·Kais DhbaibiJeanne Crassous
May 15, 2018·Journal of the American Chemical Society·Nathaniel J SchusterColin Nuckolls
May 22, 2018·Journal of the American Chemical Society·Yuki InoueShu Seki
Sep 2, 2021·The Journal of Organic Chemistry·Shunpei KataokaShin-Ichiro Kato

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