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Lignol Cleavage by Pd/C Under Mild Conditions and Without Hydrogen: A Role for Benzylic CH Activation?
Author(s) -
Zhou Xiaoyuan,
Mitra Joyee,
Rauchfuss Thomas B.
Publication year - 2014
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201301253
Subject(s) - cleavage (geology) , chemistry , hydrogen , hydrogen atom , catalysis , photochemistry , redox , bond cleavage , hydrogen storage , substrate (aquarium) , lignin , combinatorial chemistry , inorganic chemistry , organic chemistry , materials science , alkyl , oceanography , fracture (geology) , composite material , geology
Abstract The cleavage of CO bonds in lignin model compounds without hydrogen was developed using the commercially available Pd/C. Hydrogen donor solvents are helpful for this reaction through transfer hydrogenation, but not necessary. A redox neutral process that utilizes the internal hydrogen source for the cleavage is also possible. An initial mechanistic study indicates that the β‐benzylic‐H atom in the substrate plays a critical role and that the present system undergoes a process different from previous reports.