Catalytic epoxidation and 1,2-dihydroxylation of olefins with bispidine-iron(II)/H2O2 systems

Michael R. Bukowski; Peter Comba; Achim Lienke; Christian Limberg; Carlos Lopez De Laorden; Rubén Mas-Ballesté; Michael Merz; Larry Que

doi:10.1002/anie.200504357

Catalytic epoxidation and 1,2-dihydroxylation of olefins with bispidine-iron(II)/H₂O₂ systems

Michael R. Bukowski
, Peter Comba
, Achim Lienke
, Christian Limberg
, Carlos Lopez De Laorden
, Rubén Mas-Ballesté
, Michael Merz
, Larry Que

Chemistry (Twin Cities)

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

151 Scopus citations

Abstract

(Chemical Equation Presented) Going ferryl: Fe^II complexes with two isomeric bispidine ligands catalyze the oxidation of cyclooctene with H ₂O₂ in MeCN under aerobic conditions with high selectivity for the epoxide (see scheme; L = bispidine ligand). An {Fe^IV=O} complex is postulated to be the oxidant, formed by the homolytic cleavage of the O-O bond of an {Fe^III-OOH} intermediate. Performing the reaction under argon gives a mixture of cis and trans diols as well as the epoxide.

Original language	English (US)
Pages (from-to)	3446-3449
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	21
DOIs	https://doi.org/10.1002/anie.200504357
State	Published - May 19 2006

Keywords

Coordination chemistry
Dihydroxylation
Epoxidation
Homogeneous catalysis
Iron

Publisher link

10.1002/anie.200504357

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title = "Catalytic epoxidation and 1,2-dihydroxylation of olefins with bispidine-iron(II)/H2O2 systems",

abstract = "(Chemical Equation Presented) Going ferryl: FeII complexes with two isomeric bispidine ligands catalyze the oxidation of cyclooctene with H 2O2 in MeCN under aerobic conditions with high selectivity for the epoxide (see scheme; L = bispidine ligand). An \{FeIV=O\} complex is postulated to be the oxidant, formed by the homolytic cleavage of the O-O bond of an \{FeIII-OOH\} intermediate. Performing the reaction under argon gives a mixture of cis and trans diols as well as the epoxide.",

keywords = "Coordination chemistry, Dihydroxylation, Epoxidation, Homogeneous catalysis, Iron",

author = "Bukowski, \{Michael R.\} and Peter Comba and Achim Lienke and Christian Limberg and \{Lopez De Laorden\}, Carlos and Rub{\'e}n Mas-Ballest{\'e} and Michael Merz and Larry Que",

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T1 - Catalytic epoxidation and 1,2-dihydroxylation of olefins with bispidine-iron(II)/H2O2 systems

AU - Bukowski, Michael R.

AU - Comba, Peter

AU - Lienke, Achim

AU - Limberg, Christian

AU - Lopez De Laorden, Carlos

AU - Mas-Ballesté, Rubén

AU - Merz, Michael

AU - Que, Larry

PY - 2006/5/19

Y1 - 2006/5/19

N2 - (Chemical Equation Presented) Going ferryl: FeII complexes with two isomeric bispidine ligands catalyze the oxidation of cyclooctene with H 2O2 in MeCN under aerobic conditions with high selectivity for the epoxide (see scheme; L = bispidine ligand). An {FeIV=O} complex is postulated to be the oxidant, formed by the homolytic cleavage of the O-O bond of an {FeIII-OOH} intermediate. Performing the reaction under argon gives a mixture of cis and trans diols as well as the epoxide.

AB - (Chemical Equation Presented) Going ferryl: FeII complexes with two isomeric bispidine ligands catalyze the oxidation of cyclooctene with H 2O2 in MeCN under aerobic conditions with high selectivity for the epoxide (see scheme; L = bispidine ligand). An {FeIV=O} complex is postulated to be the oxidant, formed by the homolytic cleavage of the O-O bond of an {FeIII-OOH} intermediate. Performing the reaction under argon gives a mixture of cis and trans diols as well as the epoxide.

KW - Coordination chemistry

KW - Dihydroxylation

KW - Epoxidation

KW - Homogeneous catalysis

KW - Iron

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U2 - 10.1002/anie.200504357

DO - 10.1002/anie.200504357

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AN - SCOPUS:33746265814

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VL - 45

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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