Catalytic epoxidation using dioxidomolybdenum(VI) complexes with tridentate aminoalcohol phenol ligands

Md Kamal Hossain; Jörg A. Schachner; Matti Haukka; Nadia C. Mösch-Zanetti; Ebbe Nordlander; Ari Lehtonen

doi:10.1016/j.ica.2018.10.012

Catalytic epoxidation using dioxidomolybdenum(VI) complexes with tridentate aminoalcohol phenol ligands

Md Kamal Hossain, Jörg A. Schachner, Matti Haukka, Nadia C. Mösch-Zanetti, Ebbe Nordlander, Ari Lehtonen

Chemical Physics

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

Abstract

Reaction of the tridentate aminoalcohol phenol ligands 2,4-di-tert-butyl-6-(((2 hydroxyethyl)(methyl)amino)methyl)phenol (H₂L¹) and 2,4-di-tert-butyl-6-(((1-hydroxybutan-2-yl)amino)methyl)phenol (H₂L²) with [MoO₂(acac)₂] in methanol solutions resulted in the formation of [MoO₂(L¹)(MeOH)] (1) and [MoO₂(L²)(MeOH)] (3), respectively. In contrast, the analogous reactions in acetonitrile afforded the dinuclear complexes [Mo₂O₂(μ-O)₂(L¹)₂] (2) and [Mo₂O₂(μ-O)₂(L²)₂] (4). The corresponding reactions with the potentially tetradentate ligand 3-((3,5-di-tert-butyl-2-hydroxybenzyl)(methyl)amino)propane-1,2-diol (H₃L³) led to the formation of the mononuclear complex [MoO₂(L³)(MeOH)] (5) in methanol while in acetonitrile solution a trinuclear structure [Mo₃O₃(μ-O)₃(L³)₃] (6) was obtained. In both cases, the ligand moiety L³ coordinated in a tridentate fashion. The catalytic activities of complexes 1–6 in epoxidation of five different olefins, S1-5, with tert-butyl hydroperoxide and hydrogen peroxide were studied. The catalytic activities were found to be moderate to good for the reaction of substrate cis-cyclooctene S1, while all complexes were less active in the epoxidation of the more challenging substrates S2-5. The molecular structures of 1, 2, 4 and 6 were determined by single crystal X-ray diffraction analyses.

Original language	English
Pages (from-to)	17-25
Number of pages	9
Journal	Inorganica Chimica Acta
Volume	486
DOIs	https://doi.org/10.1016/j.ica.2018.10.012
Publication status	Published - 2019 Feb 24

Subject classification (UKÄ)

Inorganic Chemistry

Free keywords

Epoxidation
Molybdenum complex
Tridentate ligand
Trinuclear structure

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10.1016/j.ica.2018.10.012

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@article{4bf43a39cf3649e5990f6a778e7479a0,

title = "Catalytic epoxidation using dioxidomolybdenum(VI) complexes with tridentate aminoalcohol phenol ligands",

abstract = "Reaction of the tridentate aminoalcohol phenol ligands 2,4-di-tert-butyl-6-(((2 hydroxyethyl)(methyl)amino)methyl)phenol (H2L1) and 2,4-di-tert-butyl-6-(((1-hydroxybutan-2-yl)amino)methyl)phenol (H2L2) with [MoO2(acac)2] in methanol solutions resulted in the formation of [MoO2(L1)(MeOH)] (1) and [MoO2(L2)(MeOH)] (3), respectively. In contrast, the analogous reactions in acetonitrile afforded the dinuclear complexes [Mo2O2(μ-O)2(L1)2] (2) and [Mo2O2(μ-O)2(L2)2] (4). The corresponding reactions with the potentially tetradentate ligand 3-((3,5-di-tert-butyl-2-hydroxybenzyl)(methyl)amino)propane-1,2-diol (H3L3) led to the formation of the mononuclear complex [MoO2(L3)(MeOH)] (5) in methanol while in acetonitrile solution a trinuclear structure [Mo3O3(μ-O)3(L3)3] (6) was obtained. In both cases, the ligand moiety L3 coordinated in a tridentate fashion. The catalytic activities of complexes 1–6 in epoxidation of five different olefins, S1-5, with tert-butyl hydroperoxide and hydrogen peroxide were studied. The catalytic activities were found to be moderate to good for the reaction of substrate cis-cyclooctene S1, while all complexes were less active in the epoxidation of the more challenging substrates S2-5. The molecular structures of 1, 2, 4 and 6 were determined by single crystal X-ray diffraction analyses.",

keywords = "Epoxidation, Molybdenum complex, Tridentate ligand, Trinuclear structure",

author = "Hossain, {Md Kamal} and Schachner, {J{\"o}rg A.} and Matti Haukka and M{\"o}sch-Zanetti, {Nadia C.} and Ebbe Nordlander and Ari Lehtonen",

year = "2019",

month = feb,

day = "24",

doi = "10.1016/j.ica.2018.10.012",

language = "English",

volume = "486",

pages = "17--25",

journal = "Inorganica Chimica Acta",

issn = "0020-1693",

publisher = "Elsevier",

}

TY - JOUR

T1 - Catalytic epoxidation using dioxidomolybdenum(VI) complexes with tridentate aminoalcohol phenol ligands

AU - Hossain, Md Kamal

AU - Schachner, Jörg A.

AU - Haukka, Matti

AU - Mösch-Zanetti, Nadia C.

AU - Nordlander, Ebbe

AU - Lehtonen, Ari

PY - 2019/2/24

Y1 - 2019/2/24

N2 - Reaction of the tridentate aminoalcohol phenol ligands 2,4-di-tert-butyl-6-(((2 hydroxyethyl)(methyl)amino)methyl)phenol (H2L1) and 2,4-di-tert-butyl-6-(((1-hydroxybutan-2-yl)amino)methyl)phenol (H2L2) with [MoO2(acac)2] in methanol solutions resulted in the formation of [MoO2(L1)(MeOH)] (1) and [MoO2(L2)(MeOH)] (3), respectively. In contrast, the analogous reactions in acetonitrile afforded the dinuclear complexes [Mo2O2(μ-O)2(L1)2] (2) and [Mo2O2(μ-O)2(L2)2] (4). The corresponding reactions with the potentially tetradentate ligand 3-((3,5-di-tert-butyl-2-hydroxybenzyl)(methyl)amino)propane-1,2-diol (H3L3) led to the formation of the mononuclear complex [MoO2(L3)(MeOH)] (5) in methanol while in acetonitrile solution a trinuclear structure [Mo3O3(μ-O)3(L3)3] (6) was obtained. In both cases, the ligand moiety L3 coordinated in a tridentate fashion. The catalytic activities of complexes 1–6 in epoxidation of five different olefins, S1-5, with tert-butyl hydroperoxide and hydrogen peroxide were studied. The catalytic activities were found to be moderate to good for the reaction of substrate cis-cyclooctene S1, while all complexes were less active in the epoxidation of the more challenging substrates S2-5. The molecular structures of 1, 2, 4 and 6 were determined by single crystal X-ray diffraction analyses.

AB - Reaction of the tridentate aminoalcohol phenol ligands 2,4-di-tert-butyl-6-(((2 hydroxyethyl)(methyl)amino)methyl)phenol (H2L1) and 2,4-di-tert-butyl-6-(((1-hydroxybutan-2-yl)amino)methyl)phenol (H2L2) with [MoO2(acac)2] in methanol solutions resulted in the formation of [MoO2(L1)(MeOH)] (1) and [MoO2(L2)(MeOH)] (3), respectively. In contrast, the analogous reactions in acetonitrile afforded the dinuclear complexes [Mo2O2(μ-O)2(L1)2] (2) and [Mo2O2(μ-O)2(L2)2] (4). The corresponding reactions with the potentially tetradentate ligand 3-((3,5-di-tert-butyl-2-hydroxybenzyl)(methyl)amino)propane-1,2-diol (H3L3) led to the formation of the mononuclear complex [MoO2(L3)(MeOH)] (5) in methanol while in acetonitrile solution a trinuclear structure [Mo3O3(μ-O)3(L3)3] (6) was obtained. In both cases, the ligand moiety L3 coordinated in a tridentate fashion. The catalytic activities of complexes 1–6 in epoxidation of five different olefins, S1-5, with tert-butyl hydroperoxide and hydrogen peroxide were studied. The catalytic activities were found to be moderate to good for the reaction of substrate cis-cyclooctene S1, while all complexes were less active in the epoxidation of the more challenging substrates S2-5. The molecular structures of 1, 2, 4 and 6 were determined by single crystal X-ray diffraction analyses.

KW - Epoxidation

KW - Molybdenum complex

KW - Tridentate ligand

KW - Trinuclear structure

U2 - 10.1016/j.ica.2018.10.012

DO - 10.1016/j.ica.2018.10.012

M3 - Article

AN - SCOPUS:85055113439

SN - 0020-1693

VL - 486

SP - 17

EP - 25

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

ER -

Catalytic epoxidation using dioxidomolybdenum(VI) complexes with tridentate aminoalcohol phenol ligands

Abstract

Subject classification (UKÄ)

Free keywords

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