Benign Arylations of Dimethyl Itaconate via Heck–Matsuda Reaction Utilizing in‐Situ Generated Palladium on Aluminum Oxide

Abstract

In situ generated palladium on aluminum oxide provides an active and efficient catalytic system for the preparation of arylmethylidene succinates using the Heck-Matsuda reac- [a]

The Impact of Macrokinetic Effects on the Heck‐Matsuda Reaction Using in‐situ Generated and Immobilized Pd‐Catalysts

“…The immobilization on the carrier as well as the particle size distribution of the Pd clusters were influenced by the stirring speed. [19] In the context of optimizations with respect to the lowest possible catalyst quantities, the influence of the reaction vessel and its geometry was shown in the production of methyl 4methoxycinnamic acid ester using an in-situ generated palladium on aluminum oxide. [20] Thus, the reaction of 4-methoxybenzenediazonium tetrafluoroborate 1 with methyl acrylate using the above-mentioned catalyst with a catalyst loading of 0.1 mol% under isoperibolic conditions showed clear differences in the yield and reactivity of the reaction mixture depending on the reaction vessel used (Table 1).…”

“…Recently, we observed a significant influence of stirring speed on the catalytic activity of the system during the arylation of dimethylitaconate via Matsuda‐Heck reaction using an in‐situ generated Pd/Al 2 O 3 . The immobilization on the carrier as well as the particle size distribution of the Pd clusters were influenced by the stirring speed [19] …”

“…[3][4][5][6][7][8][9][10][11][12][13] In recent years, in-situ generated immobilized palladium catalysts have increasingly found application in this reaction. [14][15][16][17][18][19] Recently, we observed a significant influence of stirring speed on the catalytic activity of the system during the arylation of dimethylitaconate via Matsuda-Heck reaction using an in-situ generated Pd/Al 2 O 3 . The immobilization on the carrier as well as the particle size distribution of the Pd clusters were influenced by the stirring speed.…”

Heck-Matsuda reaction utilizing in-situ generated palladium on aluminum phosphate

“…High efficiency and good results have been achieved from the use of synthesized palladium/carbon catalysts [11,[14][15][16]. More recently however and based on the work of Felpin et al [17,20], we have developed efficient catalysts using Al2O3 as support. Recently, we have developed very efficient homemade catalysts using Al2O3 as support material based on the work of Felpin et al [17,20].…”

“…More recently however and based on the work of Felpin et al [17,20], we have developed efficient catalysts using Al2O3 as support. Recently, we have developed very efficient homemade catalysts using Al2O3 as support material based on the work of Felpin et al [17,20]. Using low concentrations of these catalysts and mild reaction conditions, we were able for the first time to achieve α,β,β-triarylation of methyl acrylate, single and double arylation of dimethyl itaconate in good yields.…”