Format

Send to

Choose Destination
J Am Chem Soc. 2006 Feb 22;128(7):2186-7.

Catalytic "click" rotaxanes: a substoichiometric metal-template pathway to mechanically interlocked architectures.

Author information

1
School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ, United Kingdom.

Abstract

A route to mechanically interlocked architectures that requires only a catalytic quantity of template is described. The strategy utilizes the Cu(I)-catalyzed 1,3-cycloaddition of azides with terminal alkynes. Chelating the Cu(I) to an endotopic-binding macrocycle means that the metal atom binds to the alkyne and azide in such a way that the metal-mediated bond-forming reaction occurs through the cavity of the macrocycle, forming a rotaxane. Addition of pyridine to the reaction mixture enables the Cu(I) to turn over during the reaction, permitting substoichiometric amounts of the metal to be used. The yields are very high for a rotaxane-forming reaction (up to 94% with stoichiometric Cu(I); 82% with 20 mol % of Cu(I)), and the procedure is practically simple to do (no requirement for an inert atmosphere nor dried or distilled solvents).

PMID:
16478152
DOI:
10.1021/ja056903f

Supplemental Content

Full text links

Icon for American Chemical Society
Loading ...
Support Center