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 catenates in high yields of 88-92%. Demetalation produced the corresponding 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 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%.
ASJC Scopus subject areas
- Organic Chemistry