Silicon Catalyzed C−O Bond Ring Closing Metathesis of Polyethers

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Abstract

The Lewis superacid bis(perchlorocatecholato)silane catalyzes C−O bond metathesis of alkyl ethers with an efficiency outperforming all earlier reported systems. Chemoselective ring contractions of macrocyclic crown ethers enable substrate-specific transformations, and an unprecedented ring-closing metathesis of polyethylene glycols allows polymer-selective degradation. Quantum chemical computations scrutinize a high Lewis acidity paired with a simultaneous low propensity for polydentate substrate binding as critical for successful catalysis. Based on these mechanistic insights, a second-generation class of silicon Lewis superacid with enhanced efficacy is identified and demonstrated.

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Ansmann, N., Thorwart, T., & Greb, L. (2022). Silicon Catalyzed C−O Bond Ring Closing Metathesis of Polyethers. Angewandte Chemie - International Edition, 61(44). https://doi.org/10.1002/anie.202210132

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