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Encapsulated Cobalt–Porphyrin as a Catalyst for Size‐Selective Radical‐type Cyclopropanation Reactions
Author(s) -
Otte Matthias,
Kuijpers Petrus F.,
Troeppner Oliver,
IvanovićBurmazović Ivana,
Reek Joost N. H.,
de Bruin Bas
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201400055
Subject(s) - cyclopropanation , catalysis , porphyrin , cobalt , acetone , selectivity , chemistry , reagent , aqueous solution , photochemistry , organic chemistry , inorganic chemistry
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.