Study of the nitroxyl radical catalyst in aerobic oxidative cleavage and functionalization of lignin model compounds |
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| Affiliation: | 1. Faculty of Forestry, University of Toronto, 33 Willcocks Street, Toronto, ON M5S 3B3, Canada;2. Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College Street, Toronto, ON M5S 3E5, Canada;1. Key Laboratory of Biomass Chemical Engineering of Ministry of Education, Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou, 310027 Zhejiang, China;2. Chemical & Materials Engineering Department, New Mexico State University, Las Cruces, NM 88003, USA |
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| Abstract: | The selective aerobic oxidation of hydroxyl groups, α-oxyamination of benzylic ketones, and selective cleavage of Cα-Cβ linkages in lignin model compounds were studied using nitroxyl radical catalysts and sodium nitrite. The less hindered nitroxyl radical catalysts (ABNO, 1-Me-AZADO) were found to be more reactive in comparison to TEMPO. We identified a novel method to convert α,γ-dihydroxyl β-O-4 lignin model compounds directly into corresponding α-oxyaminated products and 1,2-keto esters. A new pathway for cleavage of Cα-Cβ linkage in β-O-4 link p-hydroxyphenyl (H-units) model compounds to produce useful aromatic monomers has also been demonstrated. |
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