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Synfacts 2015; 11(1): 0097
DOI: 10.1055/s-0034-1379711
DOI: 10.1055/s-0034-1379711
Polymer-Supported Synthesis
Cyclopropanation of Alkenes with Diazoesters Using Cu@FeNPs
Ishikawa S, Hudson R, Masnadi M, Bateman M, Castonguay A, Braidy N, Moores A, * Li C.-J. * McGill University, Montreal and Université de Sherbrooke, Canada
Cyclopropanation of Diazoesters with Styrene Derivatives Catalyzed by Magnetically Recoverable Copper-Plated Iron Nanoparticles.
Tetrahedron 2014;
70: 8952-8958
Cyclopropanation of Diazoesters with Styrene Derivatives Catalyzed by Magnetically Recoverable Copper-Plated Iron Nanoparticles.
Tetrahedron 2014;
70: 8952-8958
Further Information
Publication History
Publication Date:
15 December 2014 (online)
Significance
Copper-plated iron nanoparticles (Cu@FeNPs) catalyzed the cyclopropanation of alkenes with diazoesters to give the corresponding substituted cyclopropanes in up to 76% yield (16 examples). In the reaction of 4-vinylanisole with benzyl diazoacetate, the catalyst was recovered by magnetic separation and reused four times without significant loss of catalytic activity.
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Comment
The authors reported previously the preparation of Cu@FeNPs and its application to the Huisgen reaction (Green Chem. 2012, 14, 622). ICP analysis revealed that 12 ppm of copper leached out from the fresh catalyst during the reaction. The leached copper species showed no catalytic activity.
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