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Chemo‐ and Regioselective Hydrogenolysis of Diaryl Ether C−O Bonds by a Robust Heterogeneous Ni/C Catalyst: Applications to the Cleavage of Complex Lignin‐Related Fragments
Author(s) -
Gao Fang,
Webb Jonathan D.,
Hartwig John F.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201509133
Subject(s) - hydrogenolysis , catalysis , regioselectivity , chemistry , bond cleavage , ether , nickel , lignin , organic chemistry , heterogeneous catalysis , cleavage (geology) , materials science , fracture (geology) , composite material
We report the chemo‐ and regioselective hydrogenolysis of the C−O bonds in di‐ ortho ‐substituted diaryl ethers under the catalysis of a supported nickel catalyst. The catalyst comprises heterogeneous nickel particles supported on activated carbon and furnishes arenes and phenols in high yields without hydrogenation. The high thermal stability of the embedded metal particles allows C−O bond cleavage to occur in highly substituted diaryl ether units akin to those in lignin. Preliminary mechanistic experiments show that this catalyst undergoes sintering less readily than previously reported catalyst particles that form from a solution of [Ni(cod) 2 ].