Synthesis of a rotaxane CuI triazolide under aqueous conditions

Abstract

We describe the serendipitous isolation of a stable, neutral, monomeric mechanically interlocked CuI triazolide under aqueous conditions. This "trapped" intermediate of the CuAAC catalytic cycle is sterically protected from reprotonation by the rotaxane architecture, which renders the CuI-C bond stable toward moisture and air - even carboxylic acids protonate the CuI-C bond only slowly. The isolation of this remarkably stable CuI organometallic points toward potential applications of mechanical bonding in the study of reactive intermediates. © 2013 American Chemical Society.