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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Silicon Catalyzed C−O Bond Ring Closing Metathesis of Polyethers ; day:05 ; month:10 ; year:2022 ; extent:1
Angewandte Chemie / International edition. International edition ; (05.10.2022) (gesamt 1)

Creator: Ansmann, Nils
Thorwart, Thaddäus
Greb, Lutz

DOI: 10.1002/anie.202210132

URN: urn:nbn:de:101:1-2022100615120161013764

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:35 AM CEST

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Other Objects (12)

Silicon Catalyzed C−O Bond Ring Closing Metathesis of Polyethers

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Olefin metathesis – ring-closing reaction

Carbonyl‐Alkyne Metathesis Reactions Catalyzed by Organic Halogen‐Bond Donors

Cyclopeptide Synthesis by Ring-Closing Metathesis

Highly Substrate‐Selective Macrocyclic Ring Closing Metathesis

Lewis Acid Catalyzed Carbonyl–Olefin Metathesis

Iodine‐Catalyzed Carbonyl‐Alkyne Metathesis Reactions

Selective Cross‐Metathesis Versus Ring‐Closing Metathesis of Terpenes, Taking the Path Less Travelled

Synthesis of Berkeleylactone A by Ring‐Closing Alkyne Metathesis

Synthesis of Bioactive Macrocycles Involving Ring-Closing Metathesis Strategy

SPS of Seragamide A via Relay-Ring-Closing Metathesis

Silicon Catalyzed C−O Bond Ring Closing Metathesis of Polyethers

zweidimensionales bewegtes Bild

Olefin metathesis – ring-closing reaction

Carbonyl‐Alkyne Metathesis Reactions Catalyzed by Organic Halogen‐Bond Donors

Cyclopeptide Synthesis by Ring-Closing Metathesis

Highly Substrate‐Selective Macrocyclic Ring Closing Metathesis

Lewis Acid Catalyzed Carbonyl–Olefin Metathesis

Iodine‐Catalyzed Carbonyl‐Alkyne Metathesis Reactions

Selective Cross‐Metathesis Versus Ring‐Closing Metathesis of Terpenes, Taking the Path Less Travelled

Synthesis of Berkeleylactone A by Ring‐Closing Alkyne Metathesis

Synthesis of Bioactive Macrocycles Involving Ring-Closing Metathesis Strategy

SPS of Seragamide A via Relay-Ring-Closing Metathesis

Silicon Catalyzed C−O Bond Ring Closing Metathesis of Polyethers

zweidimensionales bewegtes Bild

Olefin metathesis – ring-closing reaction

Carbonyl‐Alkyne Metathesis Reactions Catalyzed by Organic Halogen‐Bond Donors

Cyclopeptide Synthesis by Ring-Closing Metathesis

Highly Substrate‐Selective Macrocyclic Ring Closing Metathesis

Lewis Acid Catalyzed Carbonyl–Olefin Metathesis

Iodine‐Catalyzed Carbonyl‐Alkyne Metathesis Reactions

Selective Cross‐Metathesis Versus Ring‐Closing Metathesis of Terpenes, Taking the Path Less Travelled

Synthesis of Berkeleylactone A by Ring‐Closing Alkyne Metathesis

Synthesis of Bioactive Macrocycles Involving Ring-Closing Metathesis Strategy

SPS of Seragamide A via Relay-Ring-Closing Metathesis

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Silicon Catalyzed C−O Bond Ring Closing Metathesis of Polyethers

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Other Objects (12)

Silicon Catalyzed C−O Bond Ring Closing Metathesis of Polyethers

Olefin metathesis – ring-closing reaction

Carbonyl‐Alkyne Metathesis Reactions Catalyzed by Organic Halogen‐Bond Donors

Cyclopeptide Synthesis by Ring-Closing Metathesis

Highly Substrate‐Selective Macrocyclic Ring Closing Metathesis

Lewis Acid Catalyzed Carbonyl–Olefin Metathesis

Iodine‐Catalyzed Carbonyl‐Alkyne Metathesis Reactions

Selective Cross‐Metathesis Versus Ring‐Closing Metathesis of Terpenes, Taking the Path Less Travelled

Selective Cross‐Metathesis Versus Ring‐Closing Metathesis of Terpenes, Taking the Path Less Travelled

Synthesis of Berkeleylactone A by Ring‐Closing Alkyne Metathesis

Synthesis of Bioactive Macrocycles Involving Ring-Closing Metathesis Strategy

SPS of Seragamide A via Relay-Ring-Closing Metathesis

Silicon Catalyzed C−O Bond Ring Closing Metathesis of Polyethers

Olefin metathesis – ring-closing reaction

Carbonyl‐Alkyne Metathesis Reactions Catalyzed by Organic Halogen‐Bond Donors

Cyclopeptide Synthesis by Ring-Closing Metathesis

Highly Substrate‐Selective Macrocyclic Ring Closing Metathesis

Lewis Acid Catalyzed Carbonyl–Olefin Metathesis

Iodine‐Catalyzed Carbonyl‐Alkyne Metathesis Reactions

Selective Cross‐Metathesis Versus Ring‐Closing Metathesis of Terpenes, Taking the Path Less Travelled

Selective Cross‐Metathesis Versus Ring‐Closing Metathesis of Terpenes, Taking the Path Less Travelled

Synthesis of Berkeleylactone A by Ring‐Closing Alkyne Metathesis

Synthesis of Bioactive Macrocycles Involving Ring-Closing Metathesis Strategy

SPS of Seragamide A via Relay-Ring-Closing Metathesis

Silicon Catalyzed C−O Bond Ring Closing Metathesis of Polyethers

Olefin metathesis – ring-closing reaction

Carbonyl‐Alkyne Metathesis Reactions Catalyzed by Organic Halogen‐Bond Donors

Cyclopeptide Synthesis by Ring-Closing Metathesis

Highly Substrate‐Selective Macrocyclic Ring Closing Metathesis

Lewis Acid Catalyzed Carbonyl–Olefin Metathesis

Iodine‐Catalyzed Carbonyl‐Alkyne Metathesis Reactions

Selective Cross‐Metathesis Versus Ring‐Closing Metathesis of Terpenes, Taking the Path Less Travelled

Selective Cross‐Metathesis Versus Ring‐Closing Metathesis of Terpenes, Taking the Path Less Travelled

Synthesis of Berkeleylactone A by Ring‐Closing Alkyne Metathesis

Synthesis of Bioactive Macrocycles Involving Ring-Closing Metathesis Strategy

SPS of Seragamide A via Relay-Ring-Closing Metathesis

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