Synthesis of Catenane Structures via Ring-Closing Metathesis.
This study presents a detailed description of a synthetic strategy to obtain catenane architectures through ring-closing metathesis. The approach is based on phenanthroline-based ligands containing terminal olefinic units that were designed to coordinate in a tetrahedral arrangement around a copper atom. Treatment of the assembled copper complexes with ruthenium catalyst 1 resulted in [2]catenates in high yields of 88-92%. Demetalation produced the corresponding [2]catenand in nearly quantitative yields. Hydrogenation of the catenates with Crabtree's catalyst and subsequent demetalation yielded fully saturated catenands. The presently described procedure makes [2]catenanes very accessible since the synthetic route consists of six steps (Schemes 2 and 4) from commercially available 1,10-phenanthroline, the overall yield being 51%.
Weck
Marcus
M
Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, and Laboratoire de Chimie Organo-Minérale, UMR 7513 au CNRS, Faculté de Chimie, Université Louis Pasteur, 4, rue Blaise Pascal, 67070 Strasbourg.
Mohr
Bernhard
B
Sauvage
Jean-Pierre
JP
Grubbs
Robert H.
RH