Domino lignin depolymerization and reconnection to complex molecules mediated by boryl radicals. Issue 9 (22nd April 2020)

• Record Type: Journal Article
• Authors: Hong, Longcheng; Spielmeyer, Astrid; Pfeiffer, Janin; Wegner, Hermann A.
• Is Part Of: Catalysis science & technology. Volume 10:Issue 9(2020)
• Page Start: 3008
• Page End: 3014
• Publication Date: 2020-04-22
• Subjects: Catalysis -- Periodicals; 541.395
• DOI: 10.1039/d0cy00558d
• Languages: English
• ISSNs: 2044-4753

Abstract

Abstract : Lignin has been demonstrated as a source of complex molecules via a boryl-mediated domino degradation/reconnection process. Abstract : Chemical degradation of lignin has attracted increasing interest due to its potential for producing chemicals from renewable resources. Herein, we present a new transition metal free degradation procedure utilizing DDQ-oxidation and boryl radical mediated degradation, followed by reconnection of a monomer intermediate to a new dimer in a domino process. Our results include the selective degradation of oxidized β-O-4 model compounds by a boryl radical initiated with a catalytic amount of 4-(4-pyridinyl)benzonitrile and bispinacolborane B2 (pin)2 as well as its application to organosolv lignin. This sequential procedure expands the toolbox for lignin degradation from simple depolymerization to high-value products by incorporating bond forming transformations within the process, and also provides a new transition-metal free method for the construction of 1, 6-diketone fragments.