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Literature DB >> 23570328

Chemoselective metal-free aerobic alcohol oxidation in lignin.

Alireza Rahimi¹, Ali Azarpira, Hoon Kim, John Ralph, Shannon S Stahl.

Abstract

An efficient organocatalytic method for chemoselective aerobic oxidation of secondary benzylic alcohols within lignin model compounds has been identified. Extension to selective oxidation in natural lignins has also been demonstrated. The optimal catalyst system consists of 4-acetamido-TEMPO (5 mol %; TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) in combination with HNO3 and HCl (10 mol % each). Preliminary studies highlight the prospect of combining this method with a subsequent oxidation step to achieve C-C bond cleavage.

Entities: Chemical

Mesh：

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Year: 2013 PMID： 23570328 DOI： 10.1021/ja401793n

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

49 in total

1. Formic-acid-induced depolymerization of oxidized lignin to aromatics.

Authors: Alireza Rahimi; Arne Ulbrich; Joshua J Coon; Shannon S Stahl
Journal: Nature Date: 2014-11-02 Impact factor: 49.962

Review 2. Tetramethylpiperidine N-Oxyl (TEMPO), Phthalimide N-Oxyl (PINO), and Related N-Oxyl Species: Electrochemical Properties and Their Use in Electrocatalytic Reactions.

Authors: Jordan E Nutting; Mohammad Rafiee; Shannon S Stahl
Journal: Chem Rev Date: 2018-04-30 Impact factor: 60.622

3. Biomass conversion: Lignin up for break-down.

Authors: Pieter C A Bruijnincx; Bert M Weckhuysen
Journal: Nat Chem Date: 2014-12 Impact factor: 24.427

4. Electrochemical Aminoxyl-Mediated Oxidation of Primary Alcohols in Lignin to Carboxylic Acids: Polymer Modification and Depolymerization.

Authors: Mohammad Rafiee; Manar Alherech; Steven D Karlen; Shannon S Stahl
Journal: J Am Chem Soc Date: 2019-09-16 Impact factor: 15.419

Review 5. Practical aerobic oxidations of alcohols and amines with homogeneous copper/TEMPO and related catalyst systems.

Authors: Bradford L Ryland; Shannon S Stahl
Journal: Angew Chem Int Ed Engl Date: 2014-07-07 Impact factor: 15.336

Chemoselective metal-free aerobic alcohol oxidation in lignin.

1. Formic-acid-induced depolymerization of oxidized lignin to aromatics.

Review 2. Tetramethylpiperidine N-Oxyl (TEMPO), Phthalimide N-Oxyl (PINO), and Related N-Oxyl Species: Electrochemical Properties and Their Use in Electrocatalytic Reactions.

3. Biomass conversion: Lignin up for break-down.

4. Electrochemical Aminoxyl-Mediated Oxidation of Primary Alcohols in Lignin to Carboxylic Acids: Polymer Modification and Depolymerization.

Review 5. Practical aerobic oxidations of alcohols and amines with homogeneous copper/TEMPO and related catalyst systems.

6. Separation of Lignin from Corn Stover Hydrolysate with Quantitative Recovery of Ionic Liquid.

7. Bright Side of Lignin Depolymerization: Toward New Platform Chemicals.

8. Simulated moving bed chromatography: separation and recovery of sugars and ionic liquid from biomass hydrolysates.

Review 9. Quinone-Catalyzed Selective Oxidation of Organic Molecules.

Review 10. Paving the Way for Lignin Valorisation: Recent Advances in Bioengineering, Biorefining and Catalysis.