Synthesis of [2]Catenanes by Oxidative Intramolecular Diyne Coupling Mediated by Macrocyclic Copper(I) Complexes†
Correction(s) for this article
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Synthesis of [2]Catenanes by Oxidative Intramolecular Diyne Coupling Mediated by Macrocyclic Copper(I) Complexes
- Volume 48Issue 15Angewandte Chemie International Edition
- pages: 2630-2630
- First Published online: March 24, 2009
Yuta Sato
Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/sslab/
Search for more papers by this authorRyu Yamasaki Dr.
Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/sslab/
Search for more papers by this authorShinichi Saito Dr.
Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/sslab/
Search for more papers by this authorYuta Sato
Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/sslab/
Search for more papers by this authorRyu Yamasaki Dr.
Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/sslab/
Search for more papers by this authorShinichi Saito Dr.
Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/sslab/
Search for more papers by this authorWe thank the Yamada Science Foundation and the UBE Foundation for the financial support of this work.
Graphical Abstract
Right said thread: Oxidative intramolecular coupling reactions of α,ω-diynes in the presence of macrocyclic phenanthroline CuI complexes allows the synthesis of [2]catenanes in up to 64 % yield (see scheme). The bond-forming reaction leads to concurrent threading of the diyne through the phenanthroline macrocycle.
Supporting Information
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- 16The macrocyclic Cu complexes used in this study are efficient catalysts for the oxidative coupling of small alkynes such as 4-methoxyphenylacetylene and the coupling product was isolated in more than 90 % yield in the presence of a catalytic amount (10 mol %) of the complex. Therefore, in principle, the reaction of a molecule of 1 would proceed with more than two molecules of the diyne, and a multicatenane could be isolated. However, we could not isolate a multicatenane from the reaction mixture. The study directed toward the formation of the multicatenane is ongoing.
