Palladium on carbon-diethylamine-mediated hydrodeoxygenation of phenol derivatives under mild conditions

Concise Synthesis of (±)‐Aurantioclavine through a Base‐Promoted Pictet–Spengler Reaction

“…Preliminary experiments revealed that a catalytic reduction of 24 (derived from 4 and 3-methylbutanal followed by treatment with Tf 2 O in 69 % yield) with 10 % Pd-C [10] in MeOH under atmospheric pressure of hydrogen was successful in producing dihydroaurantioclavine 25 in 80 % yield (Scheme 9). [11] Nevertheless, attempted reduction of 6c under similar conditions proved to be problematic due to the susceptibility of the isobutenylamine moiety to the reduction conditions (Scheme 10). This susceptibility resulted in the generation of over-reduced product 28 ( phosphanylpropane (dppp) was performed, [12] producing 27 in low yield ( Table 2, Entry 2).…”

Total synthesis of cadalen-15-oic acid

“…Other methods for reductive hydrogenolysis 14,15 were tried in order to improve the low yield, but poor conversions and hydrolysis of sulfonate to naphthol were observed and this is definitively due to the presence of the electron-withdrawing group at the ortho position of aryl mesylate. Finally, the cadalen-15-oic acid 1 was prepared by oxidation of the resulting aldehyde 7 with sodium biphosphate, sodium chlorite and sulfamic acid.…”

Methods and Applications of Deoxygenation for the Conversion of Biomass to Petrochemical Products

“…It has also been shown that Pd on supports such as carbon, Al2O3, ZSM-5, MCM 41 [76,85,86] are active for HDO. A study conducted with benzophenone with 5% Pd on active carbon and on ZSM-5 supports proved to be very active toward hydrogenation as opposed to supports such as Al2O3, and MCM 41.…”