Triphenylsilane-fused Porphyrins

Kenichi Kato; Jun Oh Kim; Hideki Yorimitsu; Dongho Kim; Atsuhiro Osuka

doi:10.1002/asia.201600424

Triphenylsilane-fused Porphyrins

Kenichi Kato, Jun Oh Kim, Hideki Yorimitsu, Dongho Kim, Atsuhiro Osuka

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

A reaction sequence of 2-(diphenylsilyl)phenylation by Negishi coupling and intramolecular sila-Friedel–Crafts reaction has been explored for the synthesis of mono-triphenylsilane-fused porphyrins 5 M and 6 M (M= Ni, Zn) and bis-triphenylsilane-fused porphyrins 7 M and 8 Ni. A triply linked triphenylsilane-fused Ni^II porphyrin, 13 Ni, was synthesized in a stepwise manner involving the above reaction sequence and a final Pd-catalyzed C−H activating arylative cyclization. The silicon atom in 13 Ni takes a distorted planarized structure with an almost perpendicular Si-phenyl group, causing an electronic effect due to effective σ*–π* interaction.

Original language	English
Pages (from-to)	1738-1746
Number of pages	9
Journal	Chemistry - An Asian Journal
Volume	11
Issue number	11
DOIs	https://doi.org/10.1002/asia.201600424
Publication status	Published - 2016 Jun 6

Bibliographical note

Funding Information:
The work at Kyoto was supported by Grants-in-Aid from MEXT (No.: 25107002 “Science of Atomic Layers”) and from JSPS (No.: 25220802 (Scientific Research (S)), 24685007 (Young Scientists (A)), 26620081 (Exploratory Research)) and by ACT-C, JST. H.Y. thanks Kansai Research Foundation for Technology Promotion and The Asahi Glass Foundation for financial support. The research at Yonsei University was supported by the Global Research Laboratory (GRL) Program (2013K1A1A2A02050183) of the Ministry of Education, Science and Technology (MEST) of Korea.

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

Biochemistry
Organic Chemistry

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10.1002/asia.201600424

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title = "Triphenylsilane-fused Porphyrins",

abstract = "A reaction sequence of 2-(diphenylsilyl)phenylation by Negishi coupling and intramolecular sila-Friedel–Crafts reaction has been explored for the synthesis of mono-triphenylsilane-fused porphyrins 5 M and 6 M (M= Ni, Zn) and bis-triphenylsilane-fused porphyrins 7 M and 8 Ni. A triply linked triphenylsilane-fused NiII porphyrin, 13 Ni, was synthesized in a stepwise manner involving the above reaction sequence and a final Pd-catalyzed C−H activating arylative cyclization. The silicon atom in 13 Ni takes a distorted planarized structure with an almost perpendicular Si-phenyl group, causing an electronic effect due to effective σ*–π* interaction.",

author = "Kenichi Kato and Kim, {Jun Oh} and Hideki Yorimitsu and Dongho Kim and Atsuhiro Osuka",

note = "Funding Information: The work at Kyoto was supported by Grants-in-Aid from MEXT (No.: 25107002 “Science of Atomic Layers”) and from JSPS (No.: 25220802 (Scientific Research (S)), 24685007 (Young Scientists (A)), 26620081 (Exploratory Research)) and by ACT-C, JST. H.Y. thanks Kansai Research Foundation for Technology Promotion and The Asahi Glass Foundation for financial support. The research at Yonsei University was supported by the Global Research Laboratory (GRL) Program (2013K1A1A2A02050183) of the Ministry of Education, Science and Technology (MEST) of Korea. Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

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doi = "10.1002/asia.201600424",

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AU - Kim, Jun Oh

AU - Yorimitsu, Hideki

AU - Kim, Dongho

AU - Osuka, Atsuhiro

N1 - Funding Information: The work at Kyoto was supported by Grants-in-Aid from MEXT (No.: 25107002 “Science of Atomic Layers”) and from JSPS (No.: 25220802 (Scientific Research (S)), 24685007 (Young Scientists (A)), 26620081 (Exploratory Research)) and by ACT-C, JST. H.Y. thanks Kansai Research Foundation for Technology Promotion and The Asahi Glass Foundation for financial support. The research at Yonsei University was supported by the Global Research Laboratory (GRL) Program (2013K1A1A2A02050183) of the Ministry of Education, Science and Technology (MEST) of Korea. Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2016/6/6

Y1 - 2016/6/6

N2 - A reaction sequence of 2-(diphenylsilyl)phenylation by Negishi coupling and intramolecular sila-Friedel–Crafts reaction has been explored for the synthesis of mono-triphenylsilane-fused porphyrins 5 M and 6 M (M= Ni, Zn) and bis-triphenylsilane-fused porphyrins 7 M and 8 Ni. A triply linked triphenylsilane-fused NiII porphyrin, 13 Ni, was synthesized in a stepwise manner involving the above reaction sequence and a final Pd-catalyzed C−H activating arylative cyclization. The silicon atom in 13 Ni takes a distorted planarized structure with an almost perpendicular Si-phenyl group, causing an electronic effect due to effective σ*–π* interaction.

AB - A reaction sequence of 2-(diphenylsilyl)phenylation by Negishi coupling and intramolecular sila-Friedel–Crafts reaction has been explored for the synthesis of mono-triphenylsilane-fused porphyrins 5 M and 6 M (M= Ni, Zn) and bis-triphenylsilane-fused porphyrins 7 M and 8 Ni. A triply linked triphenylsilane-fused NiII porphyrin, 13 Ni, was synthesized in a stepwise manner involving the above reaction sequence and a final Pd-catalyzed C−H activating arylative cyclization. The silicon atom in 13 Ni takes a distorted planarized structure with an almost perpendicular Si-phenyl group, causing an electronic effect due to effective σ*–π* interaction.

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Triphenylsilane-fused Porphyrins

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