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, Stephen Kyalo Kanyiva, Takanori Shibata

Research output: Contribution to journalArticle

2 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 languageEnglish
Pages (from-to)15173-15177
Number of pages5
JournalChemistry - A European Journal
Volume24
Issue number57
DOIs
Publication statusPublished - 2018 Oct 12

Fingerprint

Alkenes
Olefins
Chemical activation
fluoranthene

Keywords

  • biphenylene
  • C−C bond activation
  • hydrocarbons
  • regioselective
  • rhodium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

@article{ba8bd01b71a147189170de42da310ffc,
title = "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 = "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 = "biphenylene, C−C bond activation, hydrocarbons, regioselective, rhodium",
author = "Hideaki Takano and Takeharu Ito and Kanyiva, {Stephen Kyalo} and Takanori Shibata",
year = "2018",
month = "10",
day = "12",
doi = "10.1002/chem.201804044",
language = "English",
volume = "24",
pages = "15173--15177",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "57",

}

TY - JOUR

T1 - Regioselective Activation of a Sterically More Hindered C−C Bond of Biphenylenes Using an Alkene as Both a Directing Group and a Reaction Moiety

AU - Takano, Hideaki

AU - Ito, Takeharu

AU - Kanyiva, Stephen Kyalo

AU - Shibata, Takanori

PY - 2018/10/12

Y1 - 2018/10/12

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.

KW - biphenylene

KW - C−C bond activation

KW - hydrocarbons

KW - regioselective

KW - rhodium

UR - http://www.scopus.com/inward/record.url?scp=85054530243&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85054530243&partnerID=8YFLogxK

U2 - 10.1002/chem.201804044

DO - 10.1002/chem.201804044

M3 - Article

VL - 24

SP - 15173

EP - 15177

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 57

ER -