Catalytic C-O bond cleavage of 2-aryloxy-1-arylethanols and its application to the depolymerization of lignin-related polymers.
A ruthenium-catalyzed, redox neutral C-O bond cleavage of 2-aryloxy-1-arylethanols was developed that yields cleavage products in 62-98% isolated yield. This reaction is applicable to breaking the key ethereal bond found in lignin-related polymers. The bond transformation proceeds by a tandem dehydrogenation/reductive ether cleavage. Initial mechanistic investigations indicate that the ether cleavage is most likely an organometallic C-O activation. A catalytic depolymerization of a lignin-related polymer quantitatively yields the corresponding monomer with no added reagent.
Nichols
Jason M
JM
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Bishop
Lee M
LM
Bergman
Robert G
RG
Ellman
Jonathan A
JA
D002384:Catalysis; D000431:Ethanol / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D008031:Lignin / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D009942:Organometallic Compounds; D000431:Ethanol; D012428:Ruthenium; D008031:Lignin