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Catalytic C-O bond cleavage of 2-aryloxy-1-arylethanols and its application to the depolymerization of lignin-related polymers.

ABSTRACT: 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.

SUBMITTER: Nichols JM

PROVIDER: S-EPMC2943869 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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Catalytic C-O bond cleavage of 2-aryloxy-1-arylethanols and its application to the depolymerization of lignin-related polymers.

Nichols Jason M JM Bishop Lee M LM Bergman Robert G RG Ellman Jonathan A JA

Journal of the American Chemical Society 20100901 36

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-relate ...[more]

PMID: 20731348

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