jo0c00827_si_001.pdf (2.53 MB)
Stereospecific Hydrogenolysis of Benzylic Alcohols over Pd/C
journal contribution
posted on 2020-05-22, 14:34 authored by Freya
M. Harvey, Christian G. BochetHydrogenolysis
of tertiary benzylic alcohols on palladium on carbon
(Pd/C) generally proceeds with inversion of configuration. However,
little is known about the hydrogenolysis mechanism of primary and
secondary benzylic alcohols. Literature precedents suggest that these
substrates may interact differently with the catalyst. To study the
mechanism, we synthesized a pair of deuterated diastereoisomers with
a chiral center at the benzylic position. Chemical derivatization
of the hydrogenolysis products showed that the reaction proceeds with
inversion of configuration for these substrates.