TY - JOUR
T1 - Anthranoxides as Highly Reactive Arynophiles for the Synthesis of Triptycenes
AU - Iwata, Takayuki
AU - Hyodo, Mizuki
AU - Fukami, Takuto
AU - Shiota, Yoshihito
AU - Yoshizawa, Kazunari
AU - Shindo, Mitsuru
N1 - Funding Information:
This work was partially supported by the JSPS KAKENHI Grant (No. JP18H02557, JP18H04418, JP18H04624, JP17K14449, JP20H04780, JP20K15283), the Asahi Glass Foundation (T.I.), Qdai‐jump Research Program Wakaba Challenge at Kyushu University (T.I.), and the IRCCS Fusion Emergent Research Program (T.I.). This work was performed under the Cooperative Research Program “Network Joint Research Center for Materials and Devices”. We thank Mr. Taisuke Matsumoto at Kyushu University for his assistance with the X‐ray crystal structure analyses.
Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2020/7/14
Y1 - 2020/7/14
N2 - We report herein an efficient method to synthesize triptycenes by the reaction of benzynes and anthranoxides, which are electron-rich and readily prepared from the corresponding anthrones. Using this method, 1,9-syn-substituted triptycenes were regioselectively obtained employing 3-methoxybenzynes. This method was also applied to synthesize pentiptycenes. A DFT study revealed that the cycloaddition of lithium anthranoxide and benzyne proceeds stepwise.
AB - We report herein an efficient method to synthesize triptycenes by the reaction of benzynes and anthranoxides, which are electron-rich and readily prepared from the corresponding anthrones. Using this method, 1,9-syn-substituted triptycenes were regioselectively obtained employing 3-methoxybenzynes. This method was also applied to synthesize pentiptycenes. A DFT study revealed that the cycloaddition of lithium anthranoxide and benzyne proceeds stepwise.
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U2 - 10.1002/chem.202002065
DO - 10.1002/chem.202002065
M3 - Article
C2 - 32432370
AN - SCOPUS:85086343672
SN - 0947-6539
VL - 26
SP - 8506
EP - 8510
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 39
ER -