Chemoselective Metal-Free Aerobic Alcohol Oxidation in Lignin

2013634 citationsJournal Article

Authors

Alireza Rahimi · University of Wisconsin–Madison

Ali Azarpira · Great Lakes Bioenergy Research Center

Hoon Kim · Great Lakes Bioenergy Research Center

John Ralph · Great Lakes Bioenergy Research Center

Shannon S. Stahl · University of Wisconsin–Madison

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.

Topics & Keywords

Oxidative Organic Chemistry Reactions Lignin and Wood Chemistry Mesoporous Materials and Catalysis

UN Sustainable Development Goals

Clean water and sanitation

Publication Details

Published in: Journal of the American Chemical Society

Volume 135, Issue 17, pp. 6415-6418

DOI: 10.1021/ja401793n

Field-Weighted Citation Impact: 26.35