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Literature DB >> 29781011

Homolytic cleavage of peroxide bonds via a single electron transfer of a frustrated Lewis pair.

Liu Leo Liu¹, Levy L Cao¹, Diya Zhu¹, Jiliang Zhou¹, Douglas W Stephan¹.

Abstract

Single electron transfer (SET) reactions are effected by the combination of a Mes3P/B(C6F5)3 frustrated Lewis pair with benzoyl peroxide derivatives. The resulting homolytic cleavage of the peroxide bonds affords the radical salts [Mes3P˙]+[RCOOB(C6F5)3]- (R = Ph 1, p-BrC6H42, p-MeC6H43). These species react with Ph3SnH to give [Mes3PH]+[RCOOB(C6F5)3]- (R = Ph 10, p-BrC6H411, p-MeC6H412) and (Ph3Sn)2. The mechanism of these SET reactions is discussed in light of control experiments and DFT calculations.

Entities: Chemical

Year: 2018 PMID： 29781011 DOI： 10.1039/c8cc03522a

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

7 in total

1. Optimizing the Energetics of FLP-Type H₂ Activation by Modulating the Electronic and Structural Properties of the Lewis Acids: A DFT Study.

Authors: Mojgan Heshmat; Bernd Ensing
Journal: J Phys Chem A Date: 2020-07-29 Impact factor: 2.781

2. A New Mode of Chemical Reactivity for Metal-Free Hydrogen Activation by Lewis Acidic Boranes.

Authors: Elliot L Bennett; Elliot J Lawrence; Robin J Blagg; Anna S Mullen; Fraser MacMillan; Andreas W Ehlers; Daniel J Scott; Joshua S Sapsford; Andrew E Ashley; Gregory G Wildgoose; J Chris Slootweg
Journal: Angew Chem Int Ed Engl Date: 2019-05-13 Impact factor: 15.336

Homolytic cleavage of peroxide bonds via a single electron transfer of a frustrated Lewis pair.

1. Optimizing the Energetics of FLP-Type H₂ Activation by Modulating the Electronic and Structural Properties of the Lewis Acids: A DFT Study.

2. A New Mode of Chemical Reactivity for Metal-Free Hydrogen Activation by Lewis Acidic Boranes.

3. Piers' Borane-Induced Tetramerization of Arylacetylenes.

4. SET processes in Lewis acid-base reactions: the tritylation of N-heterocyclic carbenes.

5. Facile Synthesis of a Stable Side-on Phosphinyne Complex by Redox Driven Intramolecular Cyclisation.

Review 6. Main-Group Metal Complexes in Selective Bond Formations Through Radical Pathways.

7. Single-Electron Transfer in Frustrated Lewis Pair Chemistry.

Homolytic cleavage of peroxide bonds via a single electron transfer of a frustrated Lewis pair.

1. Optimizing the Energetics of FLP-Type H2 Activation by Modulating the Electronic and Structural Properties of the Lewis Acids: A DFT Study.

2. A New Mode of Chemical Reactivity for Metal-Free Hydrogen Activation by Lewis Acidic Boranes.

3. Piers' Borane-Induced Tetramerization of Arylacetylenes.

4. SET processes in Lewis acid-base reactions: the tritylation of N-heterocyclic carbenes.

5. Facile Synthesis of a Stable Side-on Phosphinyne Complex by Redox Driven Intramolecular Cyclisation.

Review 6. Main-Group Metal Complexes in Selective Bond Formations Through Radical Pathways.

7. Single-Electron Transfer in Frustrated Lewis Pair Chemistry.

1. Optimizing the Energetics of FLP-Type H₂ Activation by Modulating the Electronic and Structural Properties of the Lewis Acids: A DFT Study.