Benzene-Fused Azacorannulene Bearing an Internal Nitrogen Atom

Shingo Ito; Yuki Tokimaru; Kyoko Nozaki

doi:10.1002/anie.201502599

Benzene-Fused Azacorannulene Bearing an Internal Nitrogen Atom

Shingo Ito^*, Yuki Tokimaru, Kyoko Nozaki

^*Corresponding author for this work

The University of Tokyo

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

180 Citations (Scopus)

Abstract

A novel nitrogen-doped corannulene derivative, 8-tert-butyl-6b²-azapentabenzo[bc,ef,hi,kl,no]corannulene, was synthesized by 1,3-dipolar cycloaddition of a polycyclic aromatic azomethine ylide with a diarylethyne and subsequent palladium-catalyzed intramolecular cyclization. This molecule represents the first example of a corannulene derivative bearing an internal heteroatom, and exhibits unique structural and physical properties caused by the introduction of the nitrogen atom and extended π-conjugation, as compared to the parent corannulene.

Original language	English
Pages (from-to)	7256-7260
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	25
DOIs	https://doi.org/10.1002/anie.201502599
Publication status	Published - Jun 1 2015
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

azomethine ylide
corannulenes
polycycles
supramolecular chemistry
synthetic methods

Access to Document

10.1002/anie.201502599

Cite this

@article{b7bcd59a8fd3405abc29494565a3f386,

title = "Benzene-Fused Azacorannulene Bearing an Internal Nitrogen Atom",

abstract = "A novel nitrogen-doped corannulene derivative, 8-tert-butyl-6b2-azapentabenzo[bc,ef,hi,kl,no]corannulene, was synthesized by 1,3-dipolar cycloaddition of a polycyclic aromatic azomethine ylide with a diarylethyne and subsequent palladium-catalyzed intramolecular cyclization. This molecule represents the first example of a corannulene derivative bearing an internal heteroatom, and exhibits unique structural and physical properties caused by the introduction of the nitrogen atom and extended π-conjugation, as compared to the parent corannulene.",

keywords = "azomethine ylide, corannulenes, polycycles, supramolecular chemistry, synthetic methods",

author = "Shingo Ito and Yuki Tokimaru and Kyoko Nozaki",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

month = jun,

day = "1",

doi = "10.1002/anie.201502599",

language = "English",

volume = "54",

pages = "7256--7260",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "25",

}

TY - JOUR

T1 - Benzene-Fused Azacorannulene Bearing an Internal Nitrogen Atom

AU - Ito, Shingo

AU - Tokimaru, Yuki

AU - Nozaki, Kyoko

PY - 2015/6/1

Y1 - 2015/6/1

N2 - A novel nitrogen-doped corannulene derivative, 8-tert-butyl-6b2-azapentabenzo[bc,ef,hi,kl,no]corannulene, was synthesized by 1,3-dipolar cycloaddition of a polycyclic aromatic azomethine ylide with a diarylethyne and subsequent palladium-catalyzed intramolecular cyclization. This molecule represents the first example of a corannulene derivative bearing an internal heteroatom, and exhibits unique structural and physical properties caused by the introduction of the nitrogen atom and extended π-conjugation, as compared to the parent corannulene.

AB - A novel nitrogen-doped corannulene derivative, 8-tert-butyl-6b2-azapentabenzo[bc,ef,hi,kl,no]corannulene, was synthesized by 1,3-dipolar cycloaddition of a polycyclic aromatic azomethine ylide with a diarylethyne and subsequent palladium-catalyzed intramolecular cyclization. This molecule represents the first example of a corannulene derivative bearing an internal heteroatom, and exhibits unique structural and physical properties caused by the introduction of the nitrogen atom and extended π-conjugation, as compared to the parent corannulene.

KW - azomethine ylide

KW - corannulenes

KW - polycycles

KW - supramolecular chemistry

KW - synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=85027950002&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85027950002&partnerID=8YFLogxK

U2 - 10.1002/anie.201502599

DO - 10.1002/anie.201502599

M3 - Article

AN - SCOPUS:85027950002

SN - 1433-7851

VL - 54

SP - 7256

EP - 7260

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 25

ER -

Benzene-Fused Azacorannulene Bearing an Internal Nitrogen Atom

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

Other files and links

Fingerprint

Cite this