Encapsulated Cobalt-Porphyrin as a Catalyst for Size-Selective Radical-type Cyclopropanation Reactions

A cobalt–porphyrin catalyst encapsulated in a cubic M8L6 cage allows cyclopropanation reactions in aqueous media. The caged‐catalyst shows enhanced activities in acetone/water as compared to pure acetone. Interestingly, the M8L6 encapsulated catalyst reveals size‐selectivity. Smaller substrates more...

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Bibliographic Details
Published in:	Chemistry : a European journal Vol. 20; no. 17; pp. 4880 - 4884
Main Authors:	Otte, Matthias, Kuijpers, Petrus F., Troeppner, Oliver, Ivanović-Burmazović, Ivana, Reek, Joost N. H., de Bruin, Bas
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 22.04.2014 WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc
Subjects:	Acetone Cage Catalysis Catalysts Chemistry Chemistry, Multidisciplinary Cobalt Cobalt - administration & dosage Cobalt - chemistry cyclopropanation Cyclopropanes - administration & dosage Cyclopropanes - chemistry Encapsulation Handles homogeneous catalysis Iron Compounds - chemistry Media Models, Molecular molecular flasks Physical Sciences Porosity porphyrins Porphyrins - chemistry radical chemistry Reagents Science & Technology Sodium salts ALKENES CAGE cyclopropanation homogeneous catalysis LIGANDS cobalt CARBENE RADICALS porphyrins radical chemistry molecular flasks WATER
ISSN:	0947-6539, 1521-3765, 1521-3765
Online Access:	Get full text
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Summary:	A cobalt–porphyrin catalyst encapsulated in a cubic M8L6 cage allows cyclopropanation reactions in aqueous media. The caged‐catalyst shows enhanced activities in acetone/water as compared to pure acetone. Interestingly, the M8L6 encapsulated catalyst reveals size‐selectivity. Smaller substrates more easily penetrate through the pores of the “molecular ship‐in‐a‐bottle catalysts” and are hence converted faster than bigger substrates. In addition, N‐tosylhydrazone sodium salts are easy to handle reagents for cyclopropanation reactions under these conditions. Molecular ship‐in‐a‐bottle: A cobalt–porphyrin catalyst encapsulated in a cubic M8L6 cage allows cyclopropanation reactions in aqueous media. The caged catalyst showed enhanced activities in acetone/water as compared to pure acetone. Most remarkably, the M8L6‐encapsulated catalyst acts as a soluble, size‐selective homogeneous “molecular ship‐in‐a‐bottle” catalyst (see scheme).
Bibliography:	European Research Council - No. 202886-CatCIR ark:/67375/WNG-XLJNZ3RD-N istex:DFE5605ACE558893A4C657A2A45D7C3D9E0B19A8 Solar Technologies Go Hybrid Netherlands Organization for Scientific Research - No. NWO-CW VICI project 016.122.613 ArticleID:CHEM201400055 Alexander von Humboldt Foundation ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23
ISSN:	0947-6539 1521-3765 1521-3765
DOI:	10.1002/chem.201400055