New synthetic strategy for diporphyrins: Pinacol coupling-rearrangement

Sumito Tokuji; Chihiro Maeda; Hideki Yorimitsu; Atsuhiro Osuka

doi:10.1002/chem.201100872

New synthetic strategy for diporphyrins: Pinacol coupling-rearrangement

Sumito Tokuji, Chihiro Maeda, Hideki Yorimitsu, Atsuhiro Osuka

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

12 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 language	English
Pages (from-to)	7154-7157
Number of pages	4
Journal	Chemistry - A European Journal
Volume	17
Issue number	26
DOIs	https://doi.org/10.1002/chem.201100872
Publication status	Published - Jun 20 2011
Externally published	Yes

Keywords

acetylation
nickel
pinacol coupling-rearrangement
porphyrin
samarium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201100872

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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.",

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author = "Sumito Tokuji and Chihiro Maeda and Hideki Yorimitsu and Atsuhiro Osuka",

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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

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 26

ER -

New synthetic strategy for diporphyrins: Pinacol coupling-rearrangement

Abstract

Keywords

ASJC Scopus subject areas

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