First Sustainable Aziridination of Olefins Using Recyclable Copper-Immobilized Magnetic Nanoparticles

Mohamad Reza Khodadadi; Gwladys Pourceau; Matthieu Becuwe; Anne Wadouachi; Sylvestre Toumieux

doi:10.1055/s-0037-1611717

Synlett, Table of Contents

Synlett 2019; 30(05): 563-566
DOI: 10.1055/s-0037-1611717

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First Sustainable Aziridination of Olefins Using Recyclable Copper-Immobilized Magnetic Nanoparticles

Mohamad Reza Khodadadi

^aLaboratoire de Glycochimie, des Antimicrobiens et des Agroressources (LG2A) CNRS UMR 7378–Institut de Chimie de Picardie FR 3085, Université de Picardie Jules Verne, 33 Rue Saint Leu, 80039 Amiens Cedex, France Email: sylvestre.toumieux@u-picardie.fr

,

Gwladys Pourceau

^aLaboratoire de Glycochimie, des Antimicrobiens et des Agroressources (LG2A) CNRS UMR 7378–Institut de Chimie de Picardie FR 3085, Université de Picardie Jules Verne, 33 Rue Saint Leu, 80039 Amiens Cedex, France Email: sylvestre.toumieux@u-picardie.fr

,

Matthieu Becuwe

^bLaboratoire de Réactivité et Chimie des Solides (LRCS), CNRS UMR 7314–Institut de Chimie de Picardie FR 3085, Université de Picardie Jules Verne, 33 Rue Saint Leu, 80039 Amiens Cedex, France

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Anne Wadouachi

^aLaboratoire de Glycochimie, des Antimicrobiens et des Agroressources (LG2A) CNRS UMR 7378–Institut de Chimie de Picardie FR 3085, Université de Picardie Jules Verne, 33 Rue Saint Leu, 80039 Amiens Cedex, France Email: sylvestre.toumieux@u-picardie.fr

,

Sylvestre Toumieux*

^aLaboratoire de Glycochimie, des Antimicrobiens et des Agroressources (LG2A) CNRS UMR 7378–Institut de Chimie de Picardie FR 3085, Université de Picardie Jules Verne, 33 Rue Saint Leu, 80039 Amiens Cedex, France Email: sylvestre.toumieux@u-picardie.fr

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Abstract

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Abstract

The first copper-catalyzed aziridination of olefins using recyclable magnetic nanoparticles is described. Magnetic nanoparticles were modified with dopamine and used as a support to coordinate copper. The methodology was optimized with styrene as olefin and using [N-(p-toluenesulfonyl)imino]phenyliodinane (PhI=NTs) as nitrene source. A microwave irradiation decreased the reaction time by 4-fold compared to conventional heating method. The catalyst was recovered by simple magnetic extraction and could be reused successfully up to five times without significant loss of activity. The methodology was applied to a range of different olefins leading to moderate to excellent yields in the formation of the expected aziridine.

Key words

sustainable aziridination - magnetic nanoparticle - copper catalyst - nitrene insertion

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References

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33 General Synthetic Procedure for Aziridination To a mixture of olefin substrates (0.4 mmol), 10% Fe₃O₄-Dopa-Cu catalyst (0.04 mmol, 0.1 equiv.) in dry acetonitrile was added PhI=NTs (0.48 mmol, 1.2 equiv.) portionwise in 5 times in microwave at 70 °C under argon atmosphere, and the whole mixture was stirred until TLC showed a complete conversion (10 min to 3 h). The catalyst was removed with an external magnet and washed with dried MeCN. The solvent was removed under reduce pressure. The crude was purified by flash chromatography on silica gel using a Reveleris™ Flash System.

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