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封装的钴卟啉作为尺寸选择性自由基型环丙烷化反应的催化剂。

Encapsulated cobalt-porphyrin as a catalyst for size-selective radical-type cyclopropanation reactions.

作者信息

Otte Matthias, Kuijpers Petrus F, Troeppner Oliver, Ivanović-Burmazović Ivana, Reek Joost N H, de Bruin Bas

机构信息

Homogeneous and Supramolecular Catalysis Group, Van't Hoff Institute for Molecular Science (HIMS), University of Amsterdam (UvA), Science Park 904, 1098 XH Amsterdam (The Netherlands).

出版信息

Chemistry. 2014 Apr 22;20(17):4880-4. doi: 10.1002/chem.201400055. Epub 2014 Mar 24.

Abstract

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.

摘要

封装在立方 M8 L6 笼中的钴卟啉催化剂可在水介质中实现环丙烷化反应。与纯丙酮相比,笼状催化剂在丙酮/水中表现出更高的活性。有趣的是,M8 L6 封装的催化剂具有尺寸选择性。较小的底物更容易穿透“瓶中分子船催化剂”的孔,因此比较大的底物转化得更快。此外,在这些条件下,N-对甲苯磺酰腙钠盐是易于处理的用于环丙烷化反应的试剂。

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