Highly efficient Tsuji–Trost allylation in water catalyzed by Pd-nanoparticles

Abstract

Palladium nanoparticles stabilized by poly(vinylpyrrolidone) catalyze Tsuji-Trost allylations in water with very high turnover numbers. The di-allylation of methylene active compounds and the allylation of bio-based phenols was performed in high yield. The allylation of lignin showed a high selectivity towards the phenolic OH groups.

Application of Electrochemical Processes to Classical Iodocyclisation: Utility for Selectivity and Mechanistic Insight

“…ether. ); 1 H NMR (400 MHz, CDCl 3 ) δ=6.96–6.85 ( m , 4H, Ar H ), 6.10 ( ddt , J=17.2, 10.7, 5.4 Hz, 1H, C H =CH 2 ), 5.41 ( dq , J =17.3, 1.6 Hz, 1H, CH=C H α H β ), 5.28 ( dq , J =10.5, 1.4 Hz, 1H, CH=CH α H β ), 4.63‐4.59 ( m , 2H, C H 2 ), 3.87 ( s , 3H, C H 3 ) ppm; Data in agreement with literature …”

Palladium-Catalyzed Functionalization of Kraft Lignin: Ether Linkages through the Telomerization Reaction

“…For instance, lignin esters are accessible from the reactionw ith acid anhydrides or acyl halides in the presence of bases. Thus, the palladium-catalyzed allylation of organosolv lignin has been recently performed with allylcarbonate, [15] and it is likely that other allylic groups should be readily accessible from metal catalyzed transformations. [10,11] More specifically, allyl ethers that introduce CÀCu nsaturations within the biopolymer are interesting for furtherc hemical transformations, and have thus attracted more recent interest.…”

“…[12][13][14] More recently,t he use of catalytic andc lean reactions to allylate the hydroxyl groups in lignins has emerged as an important issue. Thus, the palladium-catalyzed allylation of organosolv lignin has been recently performed with allylcarbonate, [15] and it is likely that other allylic groups should be readily accessible from metal catalyzed transformations. In this context, we show in the present contribution that the 1,3-butadiene telomerization reaction [16] is an efficient method to functionalize phenolic/aliphatich ydroxyl groups of an industrial grade kraft lignin with allylic octadienylc hains (Scheme 1).…”

Engineered mesoporous ionic‐modified γ‐Fe2O3@hydroxyapatite decorated with palladium nanoparticles and its catalytic properties in water

“…Supported metal nanoparticles as an important class of catalysts are versatile substrates in organic synthesis . Palladium nanoparticles (Pd NPs) because of their attractive chemical and physical properties have been broadly used in the fields of coating, fuel cells, electronics, as well as catalysis . The utilization of Pd NPs in catalysis systems involves some difficulty such as agglomeration, due to their high surface energy, and problems of separation from the reaction medium which is due to their homogeneous character.…”