Update: An efficient synthesis of poly(ethylene glycol)-supported iron(II) porphyrin using a click reaction and its application for the catalytic olefination of aldehydes

Tamilselvi Chinnusamy; Valentin Rodionov; Fritz E. Kühn; Oliver Reiser

doi:10.1002/adsc.201100289

Update: An efficient synthesis of poly(ethylene glycol)-supported iron(II) porphyrin using a click reaction and its application for the catalytic olefination of aldehydes

Tamilselvi Chinnusamy, Valentin Rodionov, Fritz E. Kühn, Oliver Reiser

Associate Professorship of Molecular Catalysis

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

20 Scopus citations

Abstract

The facile synthesis of polyethylene glycol (PEG)-immobilized iron(II) porphyrin using a copper-catalyzed azide-alkyne [3+2] cycloaddition "click" reaction is reported. The prepared complex 5 (PEG-C ₅₁H ₃₉FeN ₇O) was found to be an efficient catalyst for the selective olefination of aldehydes with ethyl diazoacetate in the presence of triphenylphosphine, and afforded excellent olefin yields with high (E) selectivities. The PEG-supported catalyst 5 was readily recovered by precipitation and filtration, and was recycled through ten runs without significant activity loss.

Original language	English
Pages (from-to)	1827-1831
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	354
Issue number	9
DOIs	https://doi.org/10.1002/adsc.201100289
State	Published - 18 Jun 2012

Keywords

copper-catalyzed azide-alkyne [3+2] cycloaddition "click" reaction
CuAAC
iron porphyrin
olefination
polyethylene glycol (PEG)
supported catalysts

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10.1002/adsc.201100289

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title = "Update: An efficient synthesis of poly(ethylene glycol)-supported iron(II) porphyrin using a click reaction and its application for the catalytic olefination of aldehydes",

abstract = "The facile synthesis of polyethylene glycol (PEG)-immobilized iron(II) porphyrin using a copper-catalyzed azide-alkyne [3+2] cycloaddition {"}click{"} reaction is reported. The prepared complex 5 (PEG-C 51H 39FeN 7O) was found to be an efficient catalyst for the selective olefination of aldehydes with ethyl diazoacetate in the presence of triphenylphosphine, and afforded excellent olefin yields with high (E) selectivities. The PEG-supported catalyst 5 was readily recovered by precipitation and filtration, and was recycled through ten runs without significant activity loss.",

keywords = "copper-catalyzed azide-alkyne [3+2] cycloaddition {"}click{"} reaction, CuAAC, iron porphyrin, olefination, polyethylene glycol (PEG), supported catalysts",

author = "Tamilselvi Chinnusamy and Valentin Rodionov and K{\"u}hn, {Fritz E.} and Oliver Reiser",

year = "2012",

month = jun,

day = "18",

doi = "10.1002/adsc.201100289",

language = "English",

volume = "354",

pages = "1827--1831",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

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}

Update: An efficient synthesis of poly(ethylene glycol)-supported iron(II) porphyrin using a click reaction and its application for the catalytic olefination of aldehydes. / Chinnusamy, Tamilselvi; Rodionov, Valentin; Kühn, Fritz E. et al.
In: Advanced Synthesis and Catalysis, Vol. 354, No. 9, 18.06.2012, p. 1827-1831.

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

TY - JOUR

T1 - Update

T2 - An efficient synthesis of poly(ethylene glycol)-supported iron(II) porphyrin using a click reaction and its application for the catalytic olefination of aldehydes

AU - Chinnusamy, Tamilselvi

AU - Rodionov, Valentin

AU - Kühn, Fritz E.

AU - Reiser, Oliver

PY - 2012/6/18

Y1 - 2012/6/18

N2 - The facile synthesis of polyethylene glycol (PEG)-immobilized iron(II) porphyrin using a copper-catalyzed azide-alkyne [3+2] cycloaddition "click" reaction is reported. The prepared complex 5 (PEG-C 51H 39FeN 7O) was found to be an efficient catalyst for the selective olefination of aldehydes with ethyl diazoacetate in the presence of triphenylphosphine, and afforded excellent olefin yields with high (E) selectivities. The PEG-supported catalyst 5 was readily recovered by precipitation and filtration, and was recycled through ten runs without significant activity loss.

AB - The facile synthesis of polyethylene glycol (PEG)-immobilized iron(II) porphyrin using a copper-catalyzed azide-alkyne [3+2] cycloaddition "click" reaction is reported. The prepared complex 5 (PEG-C 51H 39FeN 7O) was found to be an efficient catalyst for the selective olefination of aldehydes with ethyl diazoacetate in the presence of triphenylphosphine, and afforded excellent olefin yields with high (E) selectivities. The PEG-supported catalyst 5 was readily recovered by precipitation and filtration, and was recycled through ten runs without significant activity loss.

KW - copper-catalyzed azide-alkyne [3+2] cycloaddition "click" reaction

KW - CuAAC

KW - iron porphyrin

KW - olefination

KW - polyethylene glycol (PEG)

KW - supported catalysts

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U2 - 10.1002/adsc.201100289

DO - 10.1002/adsc.201100289

M3 - Article

AN - SCOPUS:84862585043

SN - 1615-4150

VL - 354

SP - 1827

EP - 1831

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 9

ER -

Update: An efficient synthesis of poly(ethylene glycol)-supported iron(II) porphyrin using a click reaction and its application for the catalytic olefination of aldehydes

Abstract

Keywords

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