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

Hossain, Md Kamal LU ; Schachner, Jörg A. ; Haukka, Matti ; Mösch-Zanetti, Nadia C. ; Nordlander, Ebbe LU and Lehtonen, Ari (2019) In Inorganica Chimica Acta 486. p.17-25
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... (More)

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.

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organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Epoxidation, Molybdenum complex, Tridentate ligand, Trinuclear structure
in
Inorganica Chimica Acta
volume
486
pages
9 pages
publisher
Elsevier
external identifiers
  • scopus:85055113439
ISSN
0020-1693
DOI
10.1016/j.ica.2018.10.012
language
English
LU publication?
yes
id
4bf43a39-cf36-49e5-990f-6a778e7479a0
date added to LUP
2018-11-14 07:57:03
date last changed
2022-04-18 00:00:21
@article{4bf43a39-cf36-49e5-990f-6a778e7479a0,
  abstract     = {{<p>Reaction of the tridentate aminoalcohol phenol ligands 2,4-di-tert-butyl-6-(((2 hydroxyethyl)(methyl)amino)methyl)phenol (H<sub>2</sub>L<sup>1</sup>) and 2,4-di-tert-butyl-6-(((1-hydroxybutan-2-yl)amino)methyl)phenol (H<sub>2</sub>L<sup>2</sup>) with [MoO<sub>2</sub>(acac)<sub>2</sub>] in methanol solutions resulted in the formation of [MoO<sub>2</sub>(L<sup>1</sup>)(MeOH)] (1) and [MoO<sub>2</sub>(L<sup>2</sup>)(MeOH)] (3), respectively. In contrast, the analogous reactions in acetonitrile afforded the dinuclear complexes [Mo<sub>2</sub>O<sub>2</sub>(μ-O)<sub>2</sub>(L<sup>1</sup>)<sub>2</sub>] (2) and [Mo<sub>2</sub>O<sub>2</sub>(μ-O)<sub>2</sub>(L<sup>2</sup>)<sub>2</sub>] (4). The corresponding reactions with the potentially tetradentate ligand 3-((3,5-di-tert-butyl-2-hydroxybenzyl)(methyl)amino)propane-1,2-diol (H<sub>3</sub>L<sup>3</sup>) led to the formation of the mononuclear complex [MoO<sub>2</sub>(L<sup>3</sup>)(MeOH)] (5) in methanol while in acetonitrile solution a trinuclear structure [Mo<sub>3</sub>O<sub>3</sub>(μ-O)<sub>3</sub>(L<sup>3</sup>)<sub>3</sub>] (6) was obtained. In both cases, the ligand moiety L<sup>3</sup> 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.</p>}},
  author       = {{Hossain, Md Kamal and Schachner, Jörg A. and Haukka, Matti and Mösch-Zanetti, Nadia C. and Nordlander, Ebbe and Lehtonen, Ari}},
  issn         = {{0020-1693}},
  keywords     = {{Epoxidation; Molybdenum complex; Tridentate ligand; Trinuclear structure}},
  language     = {{eng}},
  month        = {{02}},
  pages        = {{17--25}},
  publisher    = {{Elsevier}},
  series       = {{Inorganica Chimica Acta}},
  title        = {{Catalytic epoxidation using dioxidomolybdenum(VI) complexes with tridentate aminoalcohol phenol ligands}},
  url          = {{http://dx.doi.org/10.1016/j.ica.2018.10.012}},
  doi          = {{10.1016/j.ica.2018.10.012}},
  volume       = {{486}},
  year         = {{2019}},
}