Rotaxane synthesis <i>via</i> a dynamic [2]catenane-ring-opening, axle-cleaving double cross metathesis.

ABSTRACT: Efficient routes to [2]rotaxanes are often compromised by formation of irrecoverable, non-interlocked byproducts. Herein, we report a thermodynamically steered, atom-economical strategy that couples a Cu(i)-templated, low-strain Sauvage-type [2]catenane with di-stoppered olefin via ring-opening double cross-metathesis (RO-DCM), implementing dynamic covalent chemistry to bias the system toward the most stable interlocked architecture. The transformation proceeds through ring opening of the metalated [2]catenane and its in situ "insertion" into the axle, engaging internal olefins on both partners. Optimization of metathesis parameters (Grubbs II, DCM, 40 °C) identified the stoichiometry of the di-stoppered olefin as the key lever; using ten equivalents furnished the metalated [

SUBMITTER: Cetin MM 

PROVIDER: S-EPMC12666508 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature