Two faces of a biomimetic non-heme HO-FeV=O oxidant: Olefin epoxidation versus cis-dihydroxylation

Arianna Bassan; Margareta R.A. Blomberg; Per E.M. Siegbahn; Lawrence Que

doi:10.1002/anie.200463072

Two faces of a biomimetic non-heme HO-Fe^V=O oxidant: Olefin epoxidation versus cis-dihydroxylation

Arianna Bassan, Margareta R.A. Blomberg, Per E.M. Siegbahn, Lawrence Que

Chemistry (Twin Cities)

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

97 Scopus citations

Abstract

(Figure Presented) Reactivity along two channels is shown by the HO-Fe ^V=O species responsible for Fe(tpa)-catalyzed olefin oxidation (tpa = tris(2-pyridylmethyl)amine). Attack of the oxo ligand on an olefinic carbon atom yields epoxide and attack of the hydroxo ligand affords cis-diol (see scheme). Hybrid density functional theory now demonstrates that the two processes have comparable activation energies.

Original language	English (US)
Pages (from-to)	2939-2941
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	44
Issue number	19
DOIs	https://doi.org/10.1002/anie.200463072
State	Published - May 6 2005

Keywords

Density functional calculations
Dihydroxylation
Enzyme models
Epoxidation
Iron

Publisher link

10.1002/anie.200463072

Find It

Find It at U of M Libraries

Cite this

@article{3c15a1da902043359f702327a17585f0,

title = "Two faces of a biomimetic non-heme HO-FeV=O oxidant: Olefin epoxidation versus cis-dihydroxylation",

abstract = "(Figure Presented) Reactivity along two channels is shown by the HO-Fe V=O species responsible for Fe(tpa)-catalyzed olefin oxidation (tpa = tris(2-pyridylmethyl)amine). Attack of the oxo ligand on an olefinic carbon atom yields epoxide and attack of the hydroxo ligand affords cis-diol (see scheme). Hybrid density functional theory now demonstrates that the two processes have comparable activation energies.",

keywords = "Density functional calculations, Dihydroxylation, Enzyme models, Epoxidation, Iron",

author = "Arianna Bassan and Blomberg, {Margareta R.A.} and Siegbahn, {Per E.M.} and Lawrence Que",

year = "2005",

month = may,

day = "6",

doi = "10.1002/anie.200463072",

language = "English (US)",

volume = "44",

pages = "2939--2941",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "19",

}

TY - JOUR

T1 - Two faces of a biomimetic non-heme HO-FeV=O oxidant

T2 - Olefin epoxidation versus cis-dihydroxylation

AU - Bassan, Arianna

AU - Blomberg, Margareta R.A.

AU - Siegbahn, Per E.M.

AU - Que, Lawrence

PY - 2005/5/6

Y1 - 2005/5/6

N2 - (Figure Presented) Reactivity along two channels is shown by the HO-Fe V=O species responsible for Fe(tpa)-catalyzed olefin oxidation (tpa = tris(2-pyridylmethyl)amine). Attack of the oxo ligand on an olefinic carbon atom yields epoxide and attack of the hydroxo ligand affords cis-diol (see scheme). Hybrid density functional theory now demonstrates that the two processes have comparable activation energies.

AB - (Figure Presented) Reactivity along two channels is shown by the HO-Fe V=O species responsible for Fe(tpa)-catalyzed olefin oxidation (tpa = tris(2-pyridylmethyl)amine). Attack of the oxo ligand on an olefinic carbon atom yields epoxide and attack of the hydroxo ligand affords cis-diol (see scheme). Hybrid density functional theory now demonstrates that the two processes have comparable activation energies.

KW - Density functional calculations

KW - Dihydroxylation

KW - Enzyme models

KW - Epoxidation

KW - Iron

UR - http://www.scopus.com/inward/record.url?scp=18844377203&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=18844377203&partnerID=8YFLogxK

U2 - 10.1002/anie.200463072

DO - 10.1002/anie.200463072

M3 - Article

C2 - 15812868

AN - SCOPUS:18844377203

SN - 1433-7851

VL - 44

SP - 2939

EP - 2941

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 19

ER -