A simple catalytic system based on PdCl2(CH3CN)2 in water for cross-coupling reactions using diazonium salts

UiO‐66 microcrystals catalyzed direct arylation of enol acetates and heteroarenes with aryl diazonium salts in water

“…Notably, C–H arylation reactions employing diazonium salts as the arylating reagents have been carried out under different conditions with transition metal catalysts, photocatalysts, or metal‐free catalysts . Among them, seldom reactions were performed under mild conditions nevertheless in environment friendly aqueous medium . So we firstly investigated the solvent media at room temperature of the model reaction.…”

“…With these catalysts in hand, we initially explored their catalytic activity toward the C-H arylation of enol acetates using 4-nitrobenzenediazonium tetrafluoroborate (1a) and enol acetate (2) as the substrates (Table 1). Notably, C-H arylation reactions employing diazonium salts as the arylating reagents have been carried out under different conditions with transition metal catalysts, [28,29] photocatalysts, [8,10,30,31] or metal-free catalysts. [32,33] Among them, seldom reactions were performed under mild conditions nevertheless in environment friendly aqueous medium.…”

“…[32,33] Among them, seldom reactions were performed under mild conditions nevertheless in environment friendly aqueous medium. [29] So we firstly investigated the solvent media at room temperature of the model reaction. As shown in Table 1, the solvent plays an important role in this series of reactions.…”

Carboxymethylcellulose‐supported palladium nanoparticles generated in situ from palladium(II) carboxymethylcellulose as an efficient and reusable catalyst for ligand‐ and base‐free Heck–Matsuda and Suzuki–Miyaura couplings

“…Recently, the progress of Heck–Matsuda and/or Suzuki–Miyaura reactions using aryldiazonium salts in the formation of carbon–carbon bonds has been reviewed. The traditional procedure for a Heck–Matsuda reaction generally involves catalysis using homogeneous palladium complexes including Pd(dba) 2 , 4b) Pd 2 (dba) 3 , Pd(OAc) 2 , PdCl 2 (CH 3 CN) 2 , Pd(TFA) 2 /chiral bisoxazoline ligand, palladacycle, Pd–NHC complex, Pd–phosphinous acid complexes, and so on. Pioneering studies of the Suzuki–Miyaura coupling of aryldiazonium salts with boronic acids were reported in 1996 by Genêt and co‐workers using Pd(OAc) 2 as catalyst .…”

Pd(OAc)2 catalyzed homocoupling of arenediazonium salts in ionic liquids: synthesis of symmetrical biaryls

“…1a Among various metalmediated protocols for the synthesis of biaryls, the palladium-catalyzed Suzuki coupling utilizing aryl halides, sulfonates, or triflates, and aryl-boronic acids have been widely employed. 1 The discovery of aryl-diazonium salts as highly efficient coupling partners in Pd-catalyzed reactions, 2 opened up a new chapter in diazonium ion chemistry, and prompted the development of improved methods for arylation via Suzuki-Miyaura, [3][4][5][6][7] Sonogashira, [8][9][10] and Heck reactions. [11][12] Imidazolium ILs represent ideal media for metal-mediated coupling reactions with arenediazonium salts because both ArN 2 + salts and Pd(OAc) 2 can be dissolved in the ionic liquid.…”