To refresh myself, I read a review by John E. Moses, The growing applications of click chemistry, and through my Supramolecular Chemistry textbook on catenanes.
So they start off by putting alkynes on the ends of a chain so they can be closed. Next, they throw in a copper complex, and allow the phenanthrolines to bind for 30 minutes.
Once the complex is formed, they throw in throw in a 3,5-diazide, 3, with a little bit of heat, and bam. The sulfonated bathophenanthroline, 4, is added to complex with the copper, so it can be removed from the system, leaving just the catenane system.
Normally, catenanes are produce in low yields, but the combination of the copper complex, with the 'spring-loaded' click reaction gives great yields as you can see in the figures. A control experiment without the copper only gave 7% yield and a bunch of other products.
This does not look like a very fun NMR.
Jackson D. Megiatto, David I. Schuster (2008). General Method for Synthesis of Functionalized Macrocycles and Catenanes Utilizing “Click” Chemistry Journal of the American Chemical Society DOI: 10.1021/ja8050519
Click go the azides
Around the copper complex
High-yield chemistry
Godspeed.
This posted tagged as: journals, science
Recent posts tagged as journals:
- Quadruple-clicked Catenanes
- Slushes, Nanowords and Footnotes
- Cool abstract picture of the day and a Lack of binding
