7572-98-7Relevant academic research and scientific papers
Photocatalytic Oxidation of Lignin Model Systems by Merging Visible-Light Photoredox and Palladium Catalysis
K?rk?s, Markus D.,Bosque, Irene,Matsuura, Bryan S.,Stephenson, Corey R. J.
supporting information, p. 5166 - 5169 (2016/10/14)
Lignin valorization has long been recognized as a sustainable solution for the renewable production of aromatic compounds. Two-step oxidation/reduction strategies, whereby the first oxidation step is required to "activate" lignin systems for controlled fragmentation reactions, have recently emerged as viable routes toward this goal. Herein we describe a catalytic protocol for oxidation of lignin model systems by combining photoredox and Pd catalysis. The developed dual catalytic protocol allowed the efficient oxidation of lignin model substrates at room temperature to afford the oxidized products in good to excellent yields.
Isolation of functionalized phenolic monomers through selective oxidation and CO bond cleavage of the β-O-4 linkages in Lignin
Lancefield, Christopher S.,Ojo, O. Stephen,Tran, Fanny,Westwood, Nicholas J.
, p. 258 - 262 (2015/02/19)
Functionalized phenolic monomers have been generated and isolated from an organosolv lignin through a two-step depolymerization process. Chemoselective catalytic oxidation of β-O-4 linkages promoted by the DDQ/tBuONO/ O2 system was achieved in model compounds, including polymeric models and in real lignin. The oxidized β-O-4 linkages were then cleaved on reaction with zinc. Compared to many existing methods, this protocol, which can be achieved in one pot, is highly selective, giving rise to a simple mixture of products that can be readily purified to give pure compounds. The functionality present in these products makes them potentially valuable building blocks.
Oxidation of Lignin Model Compounds Using Single-Electron-Transfer Catalysts
DiCosimo, Robert,Szabo, Hsiao-Chiung
, p. 1673 - 1679 (2007/10/02)
The single-electron-transfer oxidation of model compounds representative of the arylglycerol β-aryl ether and 1,2-diarylpropane linkages of lignin has been examined by using Co(II), Mn(II), or Co(II)/Mn(II) as catalysts.Catalytic oxidation of 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol (DMMP) in 80percent acetic acid with 500 psi of 4percent oxygen in nitrogen and at 170 deg C resulted predominantly in products of Cα-Cβ bond cleavage when using Co(II)/Mn(II) as catalyst.Cα-Cβ bond cleavage of DMMP results from an initial single-electron oxidation toproduce an intermediate aromatic radical cation; in the absence of oxygen and catalyst, acid-catalyzed β-aryl ether cleavage was the predominant reaction pathway.Dihydroanisoin (DHA) and 1,2-bis(4-methoxyphenyl)propane-1,3-diol (BMPD) were oxidized by stoichiometric quantities of Co(III) to give solely products of Cα-Cβ bond cleavage but produced only acid-catalyzed dehydration products under reaction conditions necessary for catalytic oxidation.The application of this oxidation reaction as a replacement for chlorine bleaching of paper pulp is discussed.
