Synthesis of Catenane Structures via Ring-Closing Metathesis

Citations Over TimeTop 1% of 1999 papers

Abstract

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%.

Related Papers

• → Synthesis of Catenane Structures via Ring-Closing Metathesis(1999)221 cited
• → A double ring-closing olefin metathesis approach to [3]catenanes(2008)32 cited
• → Thermal analysis of cis-(dithiocyanato)(1,10-phenanthroline-5,6-dione)(4,4′-dicarboxy-2,2′-bipyridyl)ruthenium(II) photosensitizer(2010)13 cited
• → Synthesis and Characterization of Nitroxide-Linked Ruthenium Complexes as Molecular Probes for Microheterogeneous Environments(1996)13 cited
• → Synthesis, Characterization, and Properties of Mononuclear and Dinuclear Ruthenium(II) Complexes Containing Phenanthroline and Chlorophenanthroline(2013)1 cited