Open AccessSynthesis of a Rotaxane CuI Triazolide under Aqueous Conditions
Author(s) -
Joby Winn,
Aleksandra Pinczewska,
Stephen M. Goldup
Publication year - 2013
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja407446c
Subject(s) - chemistry , rotaxane , steric effects , aqueous solution , monomer , catalysis , photochemistry , polymer chemistry , stereochemistry , molecule , combinatorial chemistry , organic chemistry , polymer , supramolecular chemistry
We describe the serendipitous isolation of a stable, neutral, monomeric mechanically interlocked Cu(I) triazolide under aqueous conditions. This "trapped" intermediate of the CuAAC catalytic cycle is sterically protected from reprotonation by the rotaxane architecture, which renders the Cu(I)-C bond stable toward moisture and air--even carboxylic acids protonate the Cu(I)-C bond only slowly. The isolation of this remarkably stable Cu(I) organometallic points toward potential applications of mechanical bonding in the study of reactive intermediates.