Reduction of Dienes and Polyenes

Tungler, Antal; Hegedũs, Lajos; Fodor, Kinga; Farkas, G.; Fürcht, Ákos; Karancsi, Zs. P.

doi:10.1002/9780470682531.pat0233

Cited by 1 publication

(1 citation statement)

References 139 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The widely used and versatile C(sp 2 )–C(sp 2 ) coupling to synthesize dienes, followed by their exhaustive hydrogenation could be considered to be an alternative approach toward saturated ring-isolated (hetero)cycles. In turn, a lot of efforts were applied to selective mono-reduction of one double bond of dienes and polyenes [ 22 , 23 , 24 , 25 ]. Notably, no optimized reaction conditions and catalysts providing high reproducibility of methods have been reported to date for these molecular patterns.…”

Section: Introductionmentioning

confidence: 99%

Screening of Palladium/Charcoal Catalysts for Hydrogenation of Diene Carboxylates with Isolated-Rings (Hetero)aliphatic Scaffold

et al. 2023

View full text Add to dashboard Cite

A series of seven palladium-containing composites, i.e., four Pd/C and three Pd(OH)2/C (Pearlman’s catalysts), was prepared using modified common approaches to deposition of Pd or hydrated PdO on charcoal. All the composites were tested in the catalytic hydrogenation of diene carboxylates with the isolated-ring scaffold, e.g., 5,6-dihydropyridine-1(2H)-carboxylates with 2-(alkoxycarbonyl)cyclopent-1-en-1-yl and hex-1-en-1-yl substituents at the C(4)-position. The performance of the composites was also studied via the hydrogenation of quinoline as a model reaction. The composites were characterized by transmission and scanning electron microscopy (TEM and SEM), powder X-ray diffraction, and low-temperature N2 adsorption. It was found that the composites containing Pd nanoparticles (NPs) of 5–40 nm size were the most efficient catalysts for the hydrogenation of dienes, providing the reduced products with up to 90% yields at p(H2) = 100 atm, T = 30 °C for 24 h. The method of Pd NPs formation had more effect on the catalyst performance than the size of the NPs. The catalytic performance of Pearlman’s catalysts (Pd(OH)2/C) in the hydrogenation of dienes was comparable to or lower than the performance of the Pd/C systems, though the Pearlman’s catalysts were more efficient in the hydrogenation of quinoline.

show abstract