TY - JOUR
T1 - Synthesis of Distorted 1,8,13-Trisilyl-9-hydroxytriptycenes by Triple Cycloaddition of Ynolates to 3-Silylbenzynes
AU - Yoshinaga, Tatsuro
AU - Fujiwara, Takumi
AU - Iwata, Takayuki
AU - Shindo, Mitsuru
N1 - Funding Information:
This work was partially supported by the JSPS KAKENHI Grant Number (No. JP18H02557, JP18H04418, JP18H04624, JP17K14449), the Asahi Glass Foundation (T.I.), Qdai‐jump Research Program Wakaba Challenge at Kyushu University (T.I.), and the MEXT Project of “Integrated Research Consortium on Chemical Sciences” (T.I.). This work was performed under the Cooperative Research Program “Network Joint Research Center for Materials and Devices.” We thank Mr. T. Matsumoto at Kyushu University for his assistance with the X‐ray crystal structure analyses.
Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2019/11/4
Y1 - 2019/11/4
N2 - 1,8,13-Trialkyl(aryl)silyl-9-hydroxytriptycenes (trisilyltriptycenes) were synthesized by the triple addition of ynolates and 3-silylbenzynes with high regioselectivity. Benzene rings in the resulting triptycenes were highly distorted where the dihedral angles between the substituents were as high as 35°. The distortion energy induced step-by-step halogenation reactions to yield halogenated triptycenes, including chiral triptycenes. The 1,8,13-trihalogenated triptycenes were then converted to 1,8,13-functionalized triptycenes.
AB - 1,8,13-Trialkyl(aryl)silyl-9-hydroxytriptycenes (trisilyltriptycenes) were synthesized by the triple addition of ynolates and 3-silylbenzynes with high regioselectivity. Benzene rings in the resulting triptycenes were highly distorted where the dihedral angles between the substituents were as high as 35°. The distortion energy induced step-by-step halogenation reactions to yield halogenated triptycenes, including chiral triptycenes. The 1,8,13-trihalogenated triptycenes were then converted to 1,8,13-functionalized triptycenes.
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U2 - 10.1002/chem.201903024
DO - 10.1002/chem.201903024
M3 - Article
C2 - 31334876
AN - SCOPUS:85071615225
VL - 25
SP - 13855
EP - 13859
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 61
ER -