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- Title
Organometallic Chirality Sensing via "Click"‐Like η<sup>6</sup>‐Arene Coordination with an Achiral Cp*Ru(II) Piano Stool Complex.
- Authors
Nelson, Eryn; Bertke, Jeffery A.; Thanzeel, F. Yushra; Wolf, Christian
- Abstract
Piano stool complexes have been studied over many years and found widespread applications in organic synthesis, catalysis, materials and drug development. We now report the first examples of quantitative chiroptical molecular recognition of chiral compounds through click‐like η6‐arene coordination with readily available half sandwich complexes. This conceptually new approach to chirality sensing is based on irreversible acetonitrile displacement of [Cp*Ru(CH3CN)3]PF6 by an aromatic target molecule, a process that is fast and complete within a few minutes at room temperature. The metal coordination coincides with characteristic circular dichroism inductions that can be easily correlated to the absolute configuration and enantiomeric ratio of the bound molecule. A relay assay that decouples the determination of the enantiomeric composition and of the total sample amount by a practical CD/UV measurement protocol was developed and successfully tested. The introduction of piano stool complexes to the chiroptical sensing realm is mechanistically unique and extends the scope of currently known methods with small‐molecule probes that require the presence of amino, alcohol, carboxylate or other privileged functional groups for binding of the target compound. A broad application range including pharmaceutically relevant multifunctional molecules and the use in chromatography‐free asymmetric reaction analysis are also demonstrated.
- Subjects
CHIRALITY; PIANO; SANDWICH construction (Materials); MOLECULAR recognition; CHIRAL recognition; CIRCULAR dichroism; ORGANIC synthesis
- Publication
Angewandte Chemie, 2024, Vol 136, Issue 26, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202404594