Heck reactions with various types of palladium complex catalysts: application of multiphase catalysis and supercritical carbon dioxide

Homogeneous versus Supported ONN Pincer‐Type Gold and Palladium Complexes: Catalytic Activity

“…[b] 2-5% catalyst, IPh (10 mmol), n-butyl acrylate (10 mmol), KOAc (20 mmol www.chemsuschem.org colloids are generated upon addition of base to a solution of the homogeneous precursor when heating the reaction mixture. [16] Indeed, upon centrifugation of the reacted mixture we could isolate palladium particles. These isolated particles were used in a new reaction and were catalytically inactive.…”

Mizoroki–Heck Reactions: Modern Solvent Systems and Reaction Techniques

“…In a screening of various tertiary phosphine and phosphite ligands, PdCl 2 [P(OC 6 H 5 ) 3 ] 2 emerged as the most suitable catalyst precursor for the arylation of ethylene in an scCO 2 -liquid biphasic system [114]. By variation of the types of ligand (from triphenylphosphane to partly and highly fluorine-substituted ones), the reaction mixture is homogeneous or biphasic depending on the pressure applied [115]. Efficient recycling of the catalyst was also achieved by extraction of the products with scCO 2 from an ionic-liquid-based system [32] (see Section 15.2.1).…”

“…The reaction was conducted at room temperature in the presence of Pd(OAc) 2 (10 mol%) and a variety of phosphine ligands: tpp, P(o-tol) 3 , P(p-tol) 3 , P(2-furyl) 3 Reports about a toluene-ethylene glycol biphasic catalytic system for a Mizoroki-Heck reaction of iodobenzene and butyl acrylate are rare [115,124]. Potassium acetate was used as a base and various catalyst precursors (Pd(OAc) 2 , PdCl 2 , Ni(OAc) 2 , Rh(CO) 2 acac, RhCl 3 , RuCl 3 , Pt(COD)Cl 2 , CoCl 2 , 1.0 mol% each) were applied in the presence of the water-soluble ligand TPPTS.…”

Pd-catalyzed Heck arylation of cycloalkenes—studies on selectivity comparing homogeneous and heterogeneous catalysts

“…The Heck reaction, a palladium-catalyzed arylation or vinylation of olefines, has become one of the most important and powerful transition-metal-catalysed transformations in organic synthesis to generate new carbon-carbon bonds [1][2][3][4][5][6][7][8]. Nowadays, this reaction has found several commercial applications for the production of fine chemicals on multi-ton scale/year [9][10][11]: e.g.…”