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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Veröffentlicht in:	Chemistry : a European journal Jg. 20; H. 17; S. 4880 - 4884
Hauptverfasser:	Otte, Matthias, Kuijpers, Petrus F., Troeppner, Oliver, Ivanović-Burmazović, Ivana, Reek, Joost N. H., de Bruin, Bas
Format:	Journal Article
Sprache:	Englisch
Veröffentlicht:	Weinheim WILEY-VCH Verlag 22.04.2014 WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc
Schlagworte:	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
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Abstract	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).
AbstractList	A cobalt-porphyrin catalyst encapsulated in a cubic M8 L6 cage allows cyclopropanation reactions in aqueous media. The caged-catalyst shows enhanced activities in acetone/water as compared to pure acetone. Interestingly, the M8 L6 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. A cobalt-porphyrin catalyst encapsulated in a cubic M sub(8)L sub(6) cage allows cyclopropanation reactions in aqueous media. The caged-catalyst shows enhanced activities in acetone/water as compared to pure acetone. Interestingly, the M sub(8)L sub(6) 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 M sub(8)L sub(6) cage allows cyclopropanation reactions in aqueous media. The caged catalyst showed enhanced activities in acetone/water as compared to pure acetone. Most remarkably, the M sub(8)L sub(6)-encapsulated catalyst acts as a soluble, size-selective homogeneous "molecular ship-in-a-bottle" catalyst (see scheme). 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. A cobalt-porphyrin catalyst encapsulated in a cubic M8 L6 cage allows cyclopropanation reactions in aqueous media. The caged-catalyst shows enhanced activities in acetone/water as compared to pure acetone. Interestingly, the M8 L6 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.A cobalt-porphyrin catalyst encapsulated in a cubic M8 L6 cage allows cyclopropanation reactions in aqueous media. The caged-catalyst shows enhanced activities in acetone/water as compared to pure acetone. Interestingly, the M8 L6 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. A cobalt–porphyrin catalyst encapsulated in a cubic M 8 L 6 cage allows cyclopropanation reactions in aqueous media. The caged‐catalyst shows enhanced activities in acetone/water as compared to pure acetone. Interestingly, the M 8 L 6 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. 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).
Author	Otte, Matthias Ivanović-Burmazović, Ivana Reek, Joost N. H. Kuijpers, Petrus F. Troeppner, Oliver de Bruin, Bas
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Keywords	ALKENES CAGE cyclopropanation homogeneous catalysis LIGANDS cobalt CARBENE RADICALS porphyrins radical chemistry molecular flasks WATER
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Chem.
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Snippet	A cobalt–porphyrin catalyst encapsulated in a cubic M8L6 cage allows cyclopropanation reactions in aqueous media. The caged‐catalyst shows enhanced activities... A cobalt–porphyrin catalyst encapsulated in a cubic M 8 L 6 cage allows cyclopropanation reactions in aqueous media. The caged‐catalyst shows enhanced... A cobalt-porphyrin catalyst encapsulated in a cubic M8L6 cage allows cyclopropanation reactions in aqueous media. The caged-catalyst shows enhanced activities... A cobalt-porphyrin catalyst encapsulated in a cubic M8 L6 cage allows cyclopropanation reactions in aqueous media. The caged-catalyst shows enhanced activities... A cobalt-porphyrin catalyst encapsulated in a cubic M sub(8)L sub(6) cage allows cyclopropanation reactions in aqueous media. The caged-catalyst shows enhanced...
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SubjectTerms	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
Title	Encapsulated Cobalt-Porphyrin as a Catalyst for Size-Selective Radical-type Cyclopropanation Reactions
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