Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 25, Issue 7, Pages 1573-1578Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.0c00536
Keywords
heterogeneous catalysis; global deprotection; glycans; total synthesis
Categories
Funding
- Irish Research Council [GOIPG/2016/998]
- Max Planck Society
- Science Foundation Ireland [13/IA/1959]
- Irish Research Council (IRC) [GOIPG/2016/998] Funding Source: Irish Research Council (IRC)
- Science Foundation Ireland (SFI) [13/IA/1959] Funding Source: Science Foundation Ireland (SFI)
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It has been demonstrated in this study that there is wide variability in the efficiency of commercial sources of palladium on carbon (Pd/C), leading to significant differences in selectivity, reaction times, and yields. The physicochemical properties of efficient catalysts for hydrogenolysis were identified as small particle size of Pd/PdO, homogeneous distribution of Pd/PdO on the carbon support, and the oxidation state of palladium, which are good predictors of catalytic efficiency. Chemists can now identify and predict a catalyst's efficiency prior to the use of valuable synthetic material and time.
Palladium-catalyzed hydrogenolysis is often the final step in challenging natural product total syntheses and a key step in industrial processes producing fine chemicals. Here, we demonstrate that there is wide variability in the efficiency of commercial sources of palladium on carbon (Pd/C) resulting in significant differences in selectivity, reaction times, and yields. We identified the physicochemical properties of efficient catalysts for hydrogenolysis: (1) small Pd/PdO particle size (2) homogeneous distribution of Pd/PdO on the carbon support, and (3) palladium oxidation state are good predictors of catalytic efficiency. Now chemists can identify and predict a catalyst's efficiency prior to the use of valuable synthetic material and time.
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