Template Assisted One‐Pot Synthesis of [2], Linear [3], and Radial [4]Catenane via Click Reaction

Abstract Design and synthesis of higher order catenane are unexpectedly complex and involve precise cooperation among the precursors overcoming competing and opposing interactions. We achieved synthesis of [2], linear [3], radial [4] in a one‐pot reaction by consecutive ring closing through click reactions. This synthesis gave three isolable products due to two, four, and six‐click reactions between suitable coupling partners. Yields of the isolate templated‐catenane decrease from lower to higher‐ordered catenane (40 %, 12 %, and 4 %), probably due to the bite angle as well as the flexibility of the reacting partners. Removal of templating cobalt(III) ion leads to the formation of fully organic [2], linear [3], and radial [4]catenane. These synthesized catenanes were purified by column chromatography and characterized by 1 H‐NMR, 13 C‐NMR, and ESI‐MS spectroscopy. The synthesized catenanes have free binding sites suitable for post‐functionalization and may be used for the synthesis of higher‐ordered catenane.