Regioselective Activation of a Sterically More Hindered C−C Bond of Biphenylenes Using an Alkene as Both a Directing Group and a Reaction Moiety

Hideaki Takano; Takeharu Ito; Kyalo Stephen Kanyiva; Takanori Shibata

doi:10.1002/chem.201804044

Regioselective Activation of a Sterically More Hindered C−C Bond of Biphenylenes Using an Alkene as Both a Directing Group and a Reaction Moiety

Hideaki Takano, Takeharu Ito, Kyalo Stephen Kanyiva, Takanori Shibata^*

^*Corresponding author for this work

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

7 Citations (Scopus)

Abstract

The Rh-catalyzed intramolecular reaction of 1-(2-vinylaryl)-substituted biphenylenes was used to construct a dihydrobenzo[b]fluoranthene skeleton. This transformation was achieved by regioselective C−C bond cleavage of a sterically more hindered biphenylene site by using alkene as both a directing group and a reaction moiety. Furthermore, we measured and analyzed the photophysical properties of the new multicyclic fused compounds.

Original language	English
Pages (from-to)	15173-15177
Number of pages	5
Journal	Chemistry - A European Journal
Volume	24
Issue number	57
DOIs	https://doi.org/10.1002/chem.201804044
Publication status	Published - 2018 Oct 12

Keywords

C−C bond activation
biphenylene
hydrocarbons
regioselective
rhodium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201804044

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abstract = "The Rh-catalyzed intramolecular reaction of 1-(2-vinylaryl)-substituted biphenylenes was used to construct a dihydrobenzo[b]fluoranthene skeleton. This transformation was achieved by regioselective C−C bond cleavage of a sterically more hindered biphenylene site by using alkene as both a directing group and a reaction moiety. Furthermore, we measured and analyzed the photophysical properties of the new multicyclic fused compounds.",

keywords = "C−C bond activation, biphenylene, hydrocarbons, regioselective, rhodium",

author = "Hideaki Takano and Takeharu Ito and Kanyiva, {Kyalo Stephen} and Takanori Shibata",

note = "Funding Information: H.T. is grateful to the Japan Society for the Promotion of Science for the fellowship support. This work was supported by Waseda University Grant for Special Research Projects. We are grateful to Umicore for generous support and a supply of [RhCl(cod)]2. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Ito, Takeharu

AU - Kanyiva, Kyalo Stephen

AU - Shibata, Takanori

N1 - Funding Information: H.T. is grateful to the Japan Society for the Promotion of Science for the fellowship support. This work was supported by Waseda University Grant for Special Research Projects. We are grateful to Umicore for generous support and a supply of [RhCl(cod)]2. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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N2 - The Rh-catalyzed intramolecular reaction of 1-(2-vinylaryl)-substituted biphenylenes was used to construct a dihydrobenzo[b]fluoranthene skeleton. This transformation was achieved by regioselective C−C bond cleavage of a sterically more hindered biphenylene site by using alkene as both a directing group and a reaction moiety. Furthermore, we measured and analyzed the photophysical properties of the new multicyclic fused compounds.

AB - The Rh-catalyzed intramolecular reaction of 1-(2-vinylaryl)-substituted biphenylenes was used to construct a dihydrobenzo[b]fluoranthene skeleton. This transformation was achieved by regioselective C−C bond cleavage of a sterically more hindered biphenylene site by using alkene as both a directing group and a reaction moiety. Furthermore, we measured and analyzed the photophysical properties of the new multicyclic fused compounds.

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KW - regioselective

KW - rhodium

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Regioselective Activation of a Sterically More Hindered C−C Bond of Biphenylenes Using an Alkene as Both a Directing Group and a Reaction Moiety

Abstract

Keywords

ASJC Scopus subject areas

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