Dioxomolybdenum(VI) compounds with α-amino acid donor ligands as catalytic precursors for the selective oxyfunctionalization of olefins

[Display omitted] •Five dioxomolybdenum α-amino acid containing compounds were investigated as catalyst precursors for the oxyfunctionalization of olefins.•All the complexes behaved as active catalysts, showing satisfying substrates conversion and high selectivity toward epoxide.•This study confirms...

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Published inMolecular catalysis Vol. 446; pp. 39 - 48
Main Authors Abdalghani, Issam, Biancalana, Lorenzo, Aschi, Massimiliano, Pampaloni, Guido, Marchetti, Fabio, Crucianelli, Marcello
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.02.2018
Subjects
cis-Dioxomolybdenum
Heterogeneous catalysis
Olefin oxidation
tert-Butyl hydroperoxide
α-Amino acid
α-Amino acid
Heterogeneous catalysis
cis-Dioxomolybdenum
Olefin oxidation
tert-Butyl hydroperoxide
Online AccessGet full text
ISSN2468-8231
2468-8231
DOI10.1016/j.mcat.2017.12.018

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Abstract [Display omitted] •Five dioxomolybdenum α-amino acid containing compounds were investigated as catalyst precursors for the oxyfunctionalization of olefins.•All the complexes behaved as active catalysts, showing satisfying substrates conversion and high selectivity toward epoxide.•This study confirms the remarkable catalytic potential of heterogeneous cis-dioxo-Mo(VI) systems for green and sustainable processes. A series of cis-dioxomolybdenum(VI) α-amino acid containing compounds I–V has been investigated as potential catalyst precursors for the mild and selective oxyfunctionalization of conjugated or unconjugated olefins like styrene, α-methylstyrene, cis-β-methylstyrene, cyclohexene and cyclooctene, using tert-butyl hydroperoxide (TBHP) as main oxidant. All the I–V complexes behaved as active heterogeneous and recyclable catalysts, showing good to quantitative conversion values of the substrate. In all cases, high selectivity toward the corresponding epoxide formation was detected. No substantial difference in terms of efficiency has been observed among the different catalysts I–V, thus confirming that the different nature of the amino acidic side-chain does not strictly affect the catalytic process. Insights into mechanistic details and reaction free energy profile of catalytic oxidations by means of quantum chemical calculations have been discussed.
AbstractList [Display omitted] •Five dioxomolybdenum α-amino acid containing compounds were investigated as catalyst precursors for the oxyfunctionalization of olefins.•All the complexes behaved as active catalysts, showing satisfying substrates conversion and high selectivity toward epoxide.•This study confirms the remarkable catalytic potential of heterogeneous cis-dioxo-Mo(VI) systems for green and sustainable processes. A series of cis-dioxomolybdenum(VI) α-amino acid containing compounds I–V has been investigated as potential catalyst precursors for the mild and selective oxyfunctionalization of conjugated or unconjugated olefins like styrene, α-methylstyrene, cis-β-methylstyrene, cyclohexene and cyclooctene, using tert-butyl hydroperoxide (TBHP) as main oxidant. All the I–V complexes behaved as active heterogeneous and recyclable catalysts, showing good to quantitative conversion values of the substrate. In all cases, high selectivity toward the corresponding epoxide formation was detected. No substantial difference in terms of efficiency has been observed among the different catalysts I–V, thus confirming that the different nature of the amino acidic side-chain does not strictly affect the catalytic process. Insights into mechanistic details and reaction free energy profile of catalytic oxidations by means of quantum chemical calculations have been discussed.
Author Marchetti, Fabio
Crucianelli, Marcello
Pampaloni, Guido
Abdalghani, Issam
Aschi, Massimiliano
Biancalana, Lorenzo
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Keywords α-Amino acid
Heterogeneous catalysis
cis-Dioxomolybdenum
Olefin oxidation
tert-Butyl hydroperoxide
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Snippet [Display omitted] •Five dioxomolybdenum α-amino acid containing compounds were investigated as catalyst precursors for the oxyfunctionalization of olefins.•All...
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StartPage 39
SubjectTerms cis-Dioxomolybdenum
Heterogeneous catalysis
Olefin oxidation
tert-Butyl hydroperoxide
α-Amino acid
Title Dioxomolybdenum(VI) compounds with α-amino acid donor ligands as catalytic precursors for the selective oxyfunctionalization of olefins
URI https://dx.doi.org/10.1016/j.mcat.2017.12.018
Volume 446
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