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• 104-55-2 3-phenyl-propenal 
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Relevant academic research and scientific papers

Undesirable deprotection of O-TBDMS groups by Pd/C-catalyzed hydrogenation and chemoselective hydrogenation using a Pd/C(en) catalyst

In general, O-TBDMS protective groups have been believed to be stable toward Pd/C-catalyzed hydrogenation conditions. In practice, however, frequent and unexpected loss of the TBDMS protective group of a variety of hydroxyl functions occurred under neutral and mild hydrogenation conditions using 10% Pd/C in MeOH. When a 10% Pd/C-ethylenediamine complex catalyst [10% Pd/C(en)] was used instead of 10% Pd/C, the undesirable problem was perfectly overcome and the chemoselective hydrogenation of reducible functionalities leaving intact the TBDMS protective group was achieved.

On the role of water in selective hydrogenation of cinnamaldehyde to cinnamyl alcohol on PtFe catalysts

A series of carbon nanotube (CNT)-supported bimetallic PtFe nanoparticles were synthesized and employed as catalysts for hydrogenation of cinnamaldehyde in pure water. A synergy between water and bimetallic PtFe catalysts has allowed the efficiently selective production of cinnamyl alcohol. With the aid of water, an initial reaction rate of >1200 h?1 and a high selectivity of >97%, as well as a good cycling stability, were achieved with a Pt3Fe/CNT catalyst under mild reaction conditions. Isotopic labeling studies and theoretic calculation results demonstrated that the water-involved hydrogen-exchange pathway occurred with a lower energy barrier, which coexisted with the pathway of direct H2 dissociation–hydrogenation. This work also suggested that water participated in the catalytic hydrogenation reaction by serving as a hydrogen-exchange bridge.

A Water/Toluene Biphasic Medium Improves Yields and Deuterium Incorporation into Alcohols in the Transfer Hydrogenation of Aldehydes

Deuterium labeling is an interesting process that leads to compounds of use in different fields. We describe the transfer hydrogenation of aldehydes and the selective C1 deuteration of the obtained alcohols in D2O, as the only deuterium source. Different aromatic, alkylic and α,β-unsaturated aldehydes were reduced in the presence of [RuCl(p-cymene)(dmbpy)]BF4, (dmbpy=4,4′-dimethyl-2,2′-bipyridine) as the pre-catalyst and HCO2Na/HCO2H as the hydrogen source. Moreover, furfural and glucose, were selectively reduced to the valuable alcohols, furfuryl alcohol and sorbitol. The processes were carried out in neat water or in a biphasic water/toluene system. The biphasic system allowed easy recycling, higher yields, and higher selective D incorporation (using D2O/toluene). The deuteration took place due to an efficient effective M–H/D+ exchange from D2O that allows the inversion of polarity of D+ (umpolung). DFT calculations that explain the catalytic behavior in water are also included.