New synthetic strategy for diporphyrins: Pinacol coupling-rearrangement

Sumito Tokuji, Chihiro Maeda, Hideki Yorimitsu, Atsuhiro Osuka

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A new peak for porphyrins! A new approach to methylene-bridged diporphyrins has been explored, which consists of SmI2-mediated pinacol coupling followed by BF3-assisted pinacol-to-pinacolone rearrangement (see scheme). Diporphyrin 1 can further undergo multiple, dehydrative C-C bond formation to yield tetrahydropentalene-fused porphyrin dimer 2 with a rigid gable structure.

Original languageEnglish
Pages (from-to)7154-7157
Number of pages4
JournalChemistry - A European Journal
Volume17
Issue number26
DOIs
Publication statusPublished - Jun 20 2011
Externally publishedYes

Fingerprint

Porphyrins
Rigid structures
Dimers
pinacolone

Keywords

  • acetylation
  • nickel
  • pinacol coupling-rearrangement
  • porphyrin
  • samarium

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

New synthetic strategy for diporphyrins : Pinacol coupling-rearrangement. / Tokuji, Sumito; Maeda, Chihiro; Yorimitsu, Hideki; Osuka, Atsuhiro.

In: Chemistry - A European Journal, Vol. 17, No. 26, 20.06.2011, p. 7154-7157.

Research output: Contribution to journalArticle

Tokuji, Sumito ; Maeda, Chihiro ; Yorimitsu, Hideki ; Osuka, Atsuhiro. / New synthetic strategy for diporphyrins : Pinacol coupling-rearrangement. In: Chemistry - A European Journal. 2011 ; Vol. 17, No. 26. pp. 7154-7157.
@article{956dd18d4cdd4bfa9229d077cc9c305f,
title = "New synthetic strategy for diporphyrins: Pinacol coupling-rearrangement",
abstract = "A new peak for porphyrins! A new approach to methylene-bridged diporphyrins has been explored, which consists of SmI2-mediated pinacol coupling followed by BF3-assisted pinacol-to-pinacolone rearrangement (see scheme). Diporphyrin 1 can further undergo multiple, dehydrative C-C bond formation to yield tetrahydropentalene-fused porphyrin dimer 2 with a rigid gable structure.",
keywords = "acetylation, nickel, pinacol coupling-rearrangement, porphyrin, samarium",
author = "Sumito Tokuji and Chihiro Maeda and Hideki Yorimitsu and Atsuhiro Osuka",
year = "2011",
month = "6",
day = "20",
doi = "10.1002/chem.201100872",
language = "English",
volume = "17",
pages = "7154--7157",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "26",

}

TY - JOUR

T1 - New synthetic strategy for diporphyrins

T2 - Pinacol coupling-rearrangement

AU - Tokuji, Sumito

AU - Maeda, Chihiro

AU - Yorimitsu, Hideki

AU - Osuka, Atsuhiro

PY - 2011/6/20

Y1 - 2011/6/20

N2 - A new peak for porphyrins! A new approach to methylene-bridged diporphyrins has been explored, which consists of SmI2-mediated pinacol coupling followed by BF3-assisted pinacol-to-pinacolone rearrangement (see scheme). Diporphyrin 1 can further undergo multiple, dehydrative C-C bond formation to yield tetrahydropentalene-fused porphyrin dimer 2 with a rigid gable structure.

AB - A new peak for porphyrins! A new approach to methylene-bridged diporphyrins has been explored, which consists of SmI2-mediated pinacol coupling followed by BF3-assisted pinacol-to-pinacolone rearrangement (see scheme). Diporphyrin 1 can further undergo multiple, dehydrative C-C bond formation to yield tetrahydropentalene-fused porphyrin dimer 2 with a rigid gable structure.

KW - acetylation

KW - nickel

KW - pinacol coupling-rearrangement

KW - porphyrin

KW - samarium

UR - http://www.scopus.com/inward/record.url?scp=79958813785&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79958813785&partnerID=8YFLogxK

U2 - 10.1002/chem.201100872

DO - 10.1002/chem.201100872

M3 - Article

C2 - 21563221

AN - SCOPUS:79958813785

VL - 17

SP - 7154

EP - 7157

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 26

ER -