Chemoselective Metal-Free Aerobic Alcohol Oxidation in Lignin
Alireza RahimiDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue,
Madison, Wisconsin 53706, United StatesAli AzarpiraDepartment of Biochemistry and
DOE Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, 1552 University Avenue, Madison, Wisconsin
53726, United StatesHoon KimDepartment of Biochemistry and
DOE Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, 1552 University Avenue, Madison, Wisconsin
53726, United StatesJohn RalphDepartment of Biochemistry and
DOE Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, 1552 University Avenue, Madison, Wisconsin
53726, United StatesShannon S. StahlDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue,
Madison, Wisconsin 53706, United States
2013en
ABI
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.
Identifiers
Citations and references
Cited by 20 references