TY - JOUR
T1 - Synthesis of Hexaazatruxenes by Consecutive N−H/C−H Coupling Using a Hypervalent Iodine Reagent and Evaluation of Their Photophysical Properties
AU - Wu, Yuchen
AU - Sasayama, Takuma
AU - Gotoh, Takahiro
AU - Ito, Mamoru
AU - Shibata, Takanori
N1 - Funding Information:
This work was supported financially by Yamada Science Foundation 2020 and Waseda University Grant for Special Research Projects (2021C‐186). We acknowledge Central Glass Co., Ltd for a generous gift of HFIP.
Funding Information:
This work was supported financially by Yamada Science Foundation 2020 and Waseda University Grant for Special Research Projects (2021C-186). We acknowledge Central Glass Co., Ltd for a generous gift of HFIP.
Publisher Copyright:
© 2022 Wiley-VCH GmbH.
PY - 2022/7/21
Y1 - 2022/7/21
N2 - Truxene is a C3-symmetric compound with characteristic photophysical properties, and it has great potential as a light-emitting material and building block. In this study, we demonstrate the synthesis of hexaazatruxenes using a two-step protocol. First, the hexaazatruxene precursors were prepared through the Buchwald-Hartwig amination of 1,3,5-tribromobenzene with commercially available or easily prepared amino-pyridine derivatives. Then, hexaazatruxenes were synthesized through consecutive N−H/C−H coupling using a hypervalent iodine reagent. To the best of our knowledge, this is the first report on the synthesis of truxenes containing more than three heteroatoms in the main skeleton.
AB - Truxene is a C3-symmetric compound with characteristic photophysical properties, and it has great potential as a light-emitting material and building block. In this study, we demonstrate the synthesis of hexaazatruxenes using a two-step protocol. First, the hexaazatruxene precursors were prepared through the Buchwald-Hartwig amination of 1,3,5-tribromobenzene with commercially available or easily prepared amino-pyridine derivatives. Then, hexaazatruxenes were synthesized through consecutive N−H/C−H coupling using a hypervalent iodine reagent. To the best of our knowledge, this is the first report on the synthesis of truxenes containing more than three heteroatoms in the main skeleton.
KW - Hypervalent compounds
KW - Nitrogen heterocycles
KW - Photoirradiation
KW - Truxenes
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U2 - 10.1002/ejoc.202200438
DO - 10.1002/ejoc.202200438
M3 - Article
AN - SCOPUS:85134541750
SN - 1434-193X
VL - 2022
JO - Justus Liebigs Annalen der Chemie
JF - Justus Liebigs Annalen der Chemie
IS - 27
M1 - e202200438
ER -