Ionically Tagged Iron Complex-Catalyzed Epoxidation of Olefins in Imidazolium-Based Ionic Liquids

被引：45

作者：

dos Santos, Marcelo R. ^{[1
,2
]}

Diniz, Julia R. ^{[1
,2
]}

Arouca, Aline M. ^{[1
,2
]}

Gomes, Alexandre F. ^{[3
]}

Gozzo, Fabio C. ^{[3
]}

Tamborim, Silvia M. ^{[4
]}

Parize, Alexandre L. ^{[5
]}

Suarez, Paulo A. Z. ^{[1
,2
]}

Neto, Brenno A. D. ^{[1
,2
]}

机构：

[1] Univ Brasilia, Lab Med & Technol Chem, Chem Inst IQ UnB, BR-70904970 Brasilia, DF, Brazil

[2] Univ Fed Santa Catarina, INCT Catalise, Dept Quim, BR-88040900 Florianopolis, SC, Brazil

[3] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP, Brazil

[4] Univ Fed Pampa, BR-96412240 Bage, RS, Brazil

[5] IQ UnB, Lab Mat & Combustiveis, BR-70910900 Brasilia, DF, Brazil

来源：

CHEMSUSCHEM | 2012年 / 5卷 / 04期

基金：

巴西圣保罗研究基金会;

关键词：

cytochromes; ionic liquids; iron; mass spectrometry; reaction mechanisms; CYTOCHROME-P450 MODEL REACTIONS; CROSS-COUPLING REACTIONS; HYDROGEN-PEROXIDE; CIS-DIHYDROXYLATION; ALKENE EPOXIDATION; ORGANIC-SYNTHESIS; PORPHYRIN; ACID; MECHANISM; OXIDANT;

D O I：

10.1002/cssc.201100453

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new ionophilic ligand and a new ionically tagged imidazolium-based iron(III) complex were synthesized and applied in the air oxidation (also hydrogen peroxide) of alkenes in imidazolium-based ionic liquids. At least ten recycling reactions were performed. The epoxidized olefin was obtained in very good yields of 8491?%. Some important mechanistic insights are also provided based on electrospray ionization quadrupoletime of flight mass spectrometry for the oxidation reaction. These results indicate that oxidations can take place by two different pathways, depending on the reaction condition: a radical or a concerted mechanism. These results contribute towards a better understanding of iron-catalyzed oxidation mechanisms.

引用

页码：716 / 726

页数：11

共 72 条

[1] An efficient biomimetic Fe-catalyzed epoxidation of olefins using hydrogen peroxide
Anilkumar, Gopinathan
Bitterlich, Bianca
Gelalcha, Feyissa Gadissa
Tse, Man Kin
Beller, Matthias
[J]. CHEMICAL COMMUNICATIONS, 2007, (03) : 289 - 291
[2] [Anonymous], ANGEW CHEM
[3] [Anonymous], 2009, ANGEW CHEM
[4] Recent Advances in Iron Catalysis in Organic Synthesis
Bauer, Eike B.
[J]. CURRENT ORGANIC CHEMISTRY, 2008, 12 (16) : 1341 - 1369
[5] Biomimetic high-valent non-heme iron oxidants for the cis-dihydroxylation and epoxidation of olefins
Bautz, Jochen
Comba, Peter
de laorden, Carlos Lopez
Menzel, Matthias
Rajaraman, Gopalan
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (42) : 8067 - 8070
[6] From miso, sake and shoyu to cosmetics:: a century of science for kojic acid
Bentley, Ronald
[J]. NATURAL PRODUCT REPORTS, 2006, 23 (06) : 1046 - 1062
[7] An Improved Iron-Catalyzed Epoxidation of Aromatic and Aliphatic Olefins with Hydrogen Peroxide as Oxidant
Bitterlich, Bianca
Schroeder, Kristin
Tse, Man Kin
Beller, Matthias
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (29) : 4867 - 4870
[8] Development of a general and efficient iron-catalyzed epoxidation with hydrogen peroxide as oxidant
Bitterlich, Bianca
Anilkumar, Gopinathan
Gelalcha, Feyissa Gadissa
Spilker, Bjoern
Grotevendt, Anne
Jackstell, Ralf
Tse, Man Kin
Beller, Matthias
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (04) : 521 - 529
[9] Iron-catalyzed reactions in organic synthesis
Bolm, C
Legros, J
Le Paih, J
Zani, L
[J]. CHEMICAL REVIEWS, 2004, 104 (12) : 6217 - 6254
[10] Bukowski M.R., 2006, Angew. Chem, V118, P3524

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